Methoxymethyl-triphenylphosphonium chloride → HCID 69261541, compound

Participants

Reaction Conditions

Reaction Steps

Combine a solution of methoxy methyl triphenyl phosphonium chloride (358 mg, 1.047 mmol) in THF (3.6 mL) with a solution of KHMDS (0.5M in toluene, 2 mL, 1.047 mmol) at 0° C. for 20-40 min. Cool the resulting orange solution to about −78° C., then add a solution of 4-(5-formyl-thiophen-2-yloxy)-benzonitrile in THF (1 mL) dropwise over about 10 min. Stir at about −78° C. for 45 min, then allow the reaction mixture to warm to room temprature and quench with H2O (5 mL). Extract the reaction mixture with ether (5 mL), wash with H2O, dry over magnesium sulfate, filter and concentrate. Purify the crude product by flash chromatography (CH2Cl2) to provide 155 mg of 4-[5-(2-methoxy-vinyl)-thiophen-2-yloxy]-benzonitrile. Redissolve the product in i-PrOH (about 0.8 mL)—H2O (about 0.8 mL) and add pTsOH.H2O (4 mg, 0.018 mmol). Stir the reaction mixture at reflux for 2-3 hours. Cool the reaction mixture to room temprature, dilute with H2O (5 mL) and extract with diethyl ether (6 mL). Wash the organic layer with sodium bicarbonate, brine, dry over magnesium sulfate, filter and concentrate under reduced pressure to give the title compound.

Provenance & Evidence