Dimethyl Sulfide → HCID 18694150, compound

Participants

Reaction Steps

A 1M solution of (CH3)2S.BH3 in dichloromethane (0.28 mol) was added dropwise to a mixture of intermediate 13-b (0.25 mol) in tetrahydrofuran (800 ml), stirred under N2 flow. About 60 ml of the solvent was removed by distillation. The reaction mixture was stirred and refluxed for 2 h. The mixture was cooled, decomposed with CH3OH (20 ml), poured out into H2O/NaOH and this mixture was extracted with CH2Cl2. The separated organic layer was washed with water, dried (MgSO4), filtered and the solvent was evaporated, yielding 59 g of (±)-6-fluoro-3,4-dihydro-8-nitro-2H-1-benzopyran-2-methanol (104% crude residue) (interm. 14-b).

Provenance & Evidence