2,2-Difluoro-5-formylbenzodioxole → (2,2-Difluoro-1,3-dioxaindan-5-yl)methanol

Participants

Reaction Conditions

Reaction Steps

A cooled (0° C.) solution of commercially available 2,2-difluorobenzo[d][1,3]dioxole-5-carbaldehyde (1.500 g; 8.06 mmol) in anh. MeOH (60 ml) was treated portionwise with NaBH4 (1.524 g; 40.29 mmol), and the resulting mixture was stirred at 0° C., under nitrogen, for 1 h. After concentration to dryness under reduced pressure, the resulting residue was treated with water (30 ml), and extracted with DCM (2×100 ml). The mixed organic layers were washed with brine, dried over anh. MgSO4, filtered, concentrated to dryness under reduced pressure, and the residue was further dried under HV affording (2,2-difluorobenzo[d][1,3]dioxol-5-yl)methanol as a colorless oil. LC-MS (conditions D): tR=0.85 min.; no ionisation.

Provenance & Evidence