Dimethyl Sulfoxide → 1-{[(Tert-butyldimethylsilyl)oxy]methyl}cyclobutane-1-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

To a round bottom flask was added DCM (5.0 mL) and oxalyl chloride (2.0 M solution in DCM, 1.36 mL, 2.71 mmol). The reaction mixture was cooled to about −78° C. To the solution was added a solution of DMSO (0.385 mL, 5.42 mmol) in DCM (1.0 mL). The mixture was stirred for about 15 min at about −78° C. and then a solution of (1-((tert-butyldimethylsilyloxy)methyl)cyclobutyl)methanol (0.500 g, 2.17 mmol, prepared using General Procedure AL with diethyl cyclobutane-1,1-dicarboxylate [Fluka], General Procedure AK with tert-butylchlorodimethylsilane) in DCM (1.0 mL) was added. The reaction mixture was allowed to stir for about 15 min and then TEA (1.82 mL, 13.0 mmol) was added. The reaction mixture was allowed to stir for about 15 min and then warmed to ambient temperature. The reaction mixture was quenched with water (25 mL) and was extracted with DCM (3×25 mL). The organics were combined, dried with MgSO4, filtered and concentrated in vacuo to give the title compound as a colorless oil (0.486 g, 98%): 1H-NMR (DMSO-d6) δ 9.71 (s, 1H), 3.87 (s, 2H), 2.27 (m, 2H), 1.93 (m, 4H), 0.90 (s, 9H), 0.08 (s, 6H).

Provenance & Evidence