Dimethyl Sulfoxide → HCID 58026141, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 15 g (0.040 mol) of (S)-6-(4-fluoro-2-hydroxymethylphenyl)-6-methyl-4-trifluoromethylhept-1-yn-4-ol in 150 mL DCM at 0° C. was added 21.3 mL of DMSO and 21.2 mL of triethylamine. The reaction was cooled to 0° C. then 19.1 g (0.12 mol) of Pyr-SO3 was added. The reaction mixture was stirred at 0° C. for 1 hour. The reaction was then quenched with 500 mL of water, acidified with 1 N HCl to pH=2, and the organic layer was separated. The aqueous phases were then extracted with DCM. The combined organic phases were washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 5-fluoro-2-((S)-3-hydroxy-1,1-dimethyl-3-trifluoromethylhex-5-ynyl)benzaldehyde as a thick yellow oil.

Provenance & Evidence