Toluene → HCID 59070418, compound

Participants

Reaction Steps

To a solution of lactone 24 (5.7 g, 12.7 mmol) in 40 mL of THF at -78° C. was added dropwise a 1.5M solution of DIBAL-H in toluene (11.5 mL, 17.2 mmol). After 2 h, the reaction was poured into 70 mL of a saturated solution of sodium potassium tartrate and was stirred for 30 min. The mixture was extracted with ethyl acetate (3×50 mL), the combined organic layers were dried over MgSO4, filtered and concentrated, and the residue was chromatographed on silica gel (1/1 hexane/ethyl acetate) to afford 4.7 g (82%) of lactol 35.

Provenance & Evidence