Dimethyl Sulfoxide → HCID 86644155, compound

Participants

Reaction Steps

A solution of methylsulfinylmethane (20.6 ml, 289 mmol) in CH2Cl2 (260 mL) at −60° C., was added dropwise to a 2M solution of oxalyl dichloride (15.2 ml, 174 mmol) in CH2Cl2 (80 mL). The mixture was stirred for 20 minutes and then a solution of ((2S,3S)-3-(methoxymethyl)-1,4-dioxaspiro[4.5]decan-2-yl)methanol (31.3 g, 145 mmol) in CH2Cl2 (80 mL) was added dropwise. The mixture was stirred for 10 minutes and then triethylamine (101 ml, 724 mmol) was slowly added. The reaction mixture was warmed to ambient temperature and water was added. When the mixture became clear, it was extracted with CH2Cl2, dried over sodium sulfate, filtered and concentrated to afford crude (2R,3S)-3-(methoxymethyl)-1,4-dioxaspiro[4.5]decane-2-carbaldehyde (34.3 g, 96.2% yield, 87% pure) which was taken on to next reaction without further purification.

Provenance & Evidence