Ethanol → HCID 15583447, compound

Participants

Reaction Conditions

Reaction Steps

2.5 ml of borane-dimethyl sulfide complex was added drop by drop to a stirred solution of 10.00 g of 5A in 30 ml of hexane under a nitrogen atmosphere at 2°-5° C. After 2 hours at 0°-10° C., 4 ml of ethanol was added. The solvent then was stripped, and the residue was dissolved in 30 ml of tetrahydrofuran. At -2° to +6° C. under a nitrogen atmosphere, 10.72 ml of 10% sodium hydroxide solution was added in portions to the stirred mixture. Then at 15°-40° C., 6.4 ml of 30% hydrogen peroxide solution was added drop by drop. The resulting mixture was warmed to 45° C. and held there for 45 minutes, then stripped of solvent. The residue was slurried with ethyl acetate. The mixture was filtered, and the filtrate was dried (MgSO4) and stripped of solvent. The residue was vacuum distilled to give 6 -((2-ethoxyethoxy)methyl)tetrahydro-2H-pyran-3-ol (5B), b.p.: 110°-112° C., 0.07 Torr.

Provenance & Evidence