Dimethyl Sulfoxide → HCID 86605055, compound

Participants

Reaction Conditions

Reaction Steps

To a flame-dried flask equipped with stir bar under nitrogen was charged anhydrous CH2Cl2 (5 mL). The flask was immersed in a cooling bath at −78° C. Oxalyl chloride (0.24 mL, 2.7 mmol) was added neat followed by DMSO (0.29 mL, 4.1 mmol) dropwise. The reaction was stirred 10 minutes at −78° C. prior to the addition of alcohol 20-5 (0.19 g, 0.7 mmol) in minimal CH2Cl2. The resulting solution was stirred an additional 1 hour at −78° C. prior to the addition of Et3N (0.76 mL, 5.4 mmol) neat and dropwise. The reaction warmed to 0° C. over 2 hour. Upon completion, the reaction solution was washed with 5% aq. NaHCO3, dried (MgSO4), filtered and concentrated. The residue was carried crude into the vinyl triflate formation: LRMS m/z (M-C(CH3)3+H) 220.1 found, 220.2 required.

Provenance & Evidence