Dimethyl Sulfoxide → 1-Phenylpent-1-yn-3-one

Temperature

-78 °C

To a solution of oxalyl chloride (0.168 mL, 1.92 mmol) in dichloromethane (2.5 mL) at −78° C. was added dimethylsulfoxide (0.231 mL, 3.26 mmol) dropwise followed by 1-phenylpent-1-yn-3-ol (61.4 mg, 0.383 mmol) in 0.5 mL of dichloromethane dropwise. The reaction mixture was stirred at −78° C. for 1 h., and triethylamine (0.534 mL, 3.83 mmol) was then added dropwise. The reaction mixture was warmed to room temperature and stirred for 1 h. The reaction mixture was diluted with dichloromethane (2.5 mL), washed with water (1 mL), washed with a saturated aqueous solution of sodium bicarbonate (1 mL), washed with brine (1 mL), and dried over anhydrous sodium sulfate. Concentration followed by purification by silica gel chromatography with hexanes/ethyl acetate (10/1) afforded 1-phenylpent-1-yn-3-one (37 mg). The compound had an HPLC ret. time=2.88 min.−Column. YMC S5 COMBISCREEN® 4.6×50 mm; Gradient time: 4 min; Flow rate=4 ml/min; Solvent A=10% MeOH−90% Water−0.2% H3PO4; Solvent B=90% MeOH−10% water−0.2% H3PO4; Start % B=0; Final % B=100. LC-MS: M+1=159+.

1. temperatureThe reaction mixture was warmed to room temperature
2. stirringstirred for 1 h
3. washwashed with water (1 mL)
4. washwashed with a saturated aqueous solution of sodium bicarbonate (1 mL)
5. washwashed with brine (1 mL)
6. dry with materialdried over anhydrous sodium sulfate
7. concentrationConcentration
8. customfollowed by purification by silica gel chromatography with hexanes/ethyl acetate (10/1)

ORD record

ord-db9e5824b79c47c7b94434667e1c1d63

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08354398B2