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Biotage® PS-Triphenylphosphine

Easy to Remove Phosphine Oxide for Mitsunobu/Wittig Reaction

ps-triphenylphosphine

Biotage® PS-Triphenylphosphine is a powerful supported phosphine reagent for popular reactions such as Wittig, Mitsunobu, chlorination of acids and alcohols and the scavenging of alkyl halides. Unlike the small molecule reagent, the triphenylphosphine oxide by-product of reaction stays 100% resin bound, meaning that removal of product from phosphine oxide can be accomplished by simple low tech filtration techniques.

CONSUMABLES

Part No. Description Product type Pack Size Price
PS-Triphenylphosphine 800378 Biotage® PS-Triphenylphosphine, 10 g Consumables 1 Log in for price
PS-Triphenylphosphine 800379 Biotage® PS-Triphenylphosphine, 25 g Consumables 1 Log in for price
PS-Triphenylphosphine 800380 Biotage® PS-Triphenylphosphine, 100 g Consumables 1 Log in for price
PS-Triphenylphosphine 800510 Biotage® PS-Triphenylphosphine, 3 g Consumables 1 Log in for price

Committed to preserving our shared environment – further details available on request.

Can be used in processes in compliance with cGMP standards.

Manufacture of consumables is accredited by the world renowned British Standards Institute.

Flexible supply chains, back up manufacturing and warehousing ensures supply risk reduction

Can be used in processes in compliance with GLP standards.

Products which are scaleable from lab or development to process scale.

Long to indefinite product shelf life, reduced process risk.

Supports pharma guidelines for reducing elemental impurities in APIs.

Further extractable information provided on request.

Raw materials certified free of materials of human or animal origin.

Chemical substances used in our manufacturing process do not require registration.

Able to withstand mechanical stirring and heating under normal reaction conditions.

Download the product note.

 

PS-Triphenylphosphine (PS-PPh3) is a polymer-bound triphenylphosphine reagent. After the reaction, triphenylphosphine oxide or other phosphine-based by-products remain 100% resin bound permitting reaction products to be chemically purified or isolated via economical low-tech separation methods such as filtration.

Major Application Areas

  • Mitsunobu chemistry - in the synthesis of aryl or alkyl ethers
  • Chlorination - for the ready conversion of alcohols and acids to the corresponding halides or acid chlorides
  • Wittig chemistry - for C=C double bond formation in the synthesis of olefins
  • Scavenging - of alkyl halides in solution
  • Cyanation - of aryl halides to form aryl cyanides
  • Cyclisation (condensation) to form 1,3,4-oxadiazoles

Representative Procedures

Mitsunobu Reaction

To a reaction vessel containing PS-Triphenylphosphine resin (311 mg, 0.66 mmol) was added a solution of p-methoxyphenol (0.45 mmol in 1 mL anhydrous THF). The suspension was allowed to stand for 5 minutes and then a solution of DBAD (di-tert-butyl azodicarboxylate) (1 mL, 0.48 mmol in anhydrous THF) was added. A further 0.5 mL of THF was added and the solution agitated at room temperature for 30 min. A solution of benzyl alcohol (1 mL, 0.3 mmol in anhydrous THF) was added and the reaction stirred overnight. In order to scavenge any excess phenols, MP-Carbonate resin (274 mg, 0.75 mmol) was then added and the mixture was stirred for a further 2 h. The resin was filtered and washed with THF (2 x 2 mL). To the filtrate was added 5 mL of a TFA/DCM/water 50:48:2) solution, and the mixture was stirred at RT for 2 h. The product was then extracted with MTBE, washed with water, and the MTBE layer concentrated to afford the product in 81% yield and 100% purity.

Wittig Reaction

1-Iodobutane (0.53 mL, 8.52 mmol) was added to a suspension of PS-Triphenylphosphine (3.0 g, 4.26 mmol) in 30 mL DMF and the reaction was stirred for 48 h at 65 °C. The resulting phosphonium resin was washed with DMF (4 x 40 mL), toluene (4 x 40 mL), DCM (4 x 40 mL), and diethyl ether (4 x 40 mL) and dried in vacuo for 12 h. The dried phosphonium resin (0.2 g, 0.2 mmol) was added to a reaction vessel, followed by the addition of THF (2 mL). To the suspension of phosphonium resin was added a solution of sodium bis(dimethylsilyl)amide (2.0 M NaHMDS in THF, 0.4 mL, 0.8 mmol) at room temperature and the reaction stirred for 1 h. The ylide resin was washed with THF (5 x 4 mL) to remove excess base. To the suspension of ylide resin in anhydrous THF (2 mL) was added a solution of p-methoxybenzaldehyde (0.2 mL, 0.1 mmol) in THF (2 mL) and the mixture was stirred for 16 h. The reaction mixture was diluted with 2 mL hexane and directly applied to a silica SPE cartridge8 followed by washing with hexane/ether (2:1, 2 x 4 mL). The solvent was concentrated to provide the olefin in 94% yield (GC purity 91%).

Chlorination

To a suspension of PS-Triphenylphosphine resin in CCl4 (1 g,2.12 mmol in 8 mL) was added a solution of piperonyl alcohol in CCl4 (152 mg, 1 mmol in 2 mL). The reaction was heated at reflux for 3 h after which the mixture was filtered and the filtrate concentrated to give pure piperonyl chloride in 100% theoretical yield and purity.

Scavenging of Alkyl Halide

PS-Triphenylphosphine (3.0 equivalents) was added to a solution of benzyl bromide (1.0 equivalent) in DMF (10 mL/g resin added) and the reaction stirred at room temperature for 5–16 h. Results by GC analysis indicate >80% scavenging after 6 h and 100% scavenging after 16 h.