Dimethyl Sulfoxide → HCID 178521035, compound

Participants

Reaction Conditions

Reaction Steps

In a 25 mL flask, a solution of dry DMSO (0.2 mL, 2.76 mmol) in 7 mL dry CH2Cl2 was cooled to −78° C., after which oxalyl chloride (0.12 mL, 1.37 mmol) was added drop by drop under argon. After stirring at −78° C. for 30 min, a CH2Cl2 solution of 1-hydroxymethyl-3-benzyloxymethyl-cyclobutane (cisl trans=211, 0.2 g, 0.97 mmol) was added drop by drop. After stirring for 1 hr, Et3N (0.7 mL, 4.9 mmol) was added dropwisely. After 15 min, the reaction was warmed to ambient temperature. After 4 hr, TLC showed no starting material. Then the reaction mixture was diluted with 30 mL CH2Cl2, washed with 30% aqueous NH4Cl (2×10 mL), H2O (1×10 mL) and brine (1×10 mL). The organic phase was dried over MgSO4 and the solvents were removed to give an oily product, which was purified by silica gel chromatography ((Hexane: EtOAc=9:1) to give the cis-diastereomer (74 mg, 37.4%, Rf=0.43 (Hexane: EtOAc=12:1)) as a colorless oil. 1H NMR (CDCl3, 400 MHz): δ 2.01-2.08 (m, 2H), 2.21-2.28 (m, 2H), 2.58-2.70 (m, 1H), 3.03-3.12 (m, 1H), 3.37-3.39 (d, J=8.0, 2H), 4.49 (s, 2H), 7.25-7.36 (m, 5H), 9.66-9.67 (d, J=4.0, 1H). MS (FAB): expected for C13H16O2 (M−H)+ 203.26. Found 203.10658. IR (neat) νmax 3054, 2935, 2858, 1704, 1454, 1266, 1092, 738, 704.

Provenance & Evidence