Ethanol → HCID 15583447, compound

Temperature

45 °C

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.

1. waitheld there for 45 minutes
2. filtrationThe mixture was filtered
3. dry with materialthe filtrate was dried (MgSO4)
4. distillationdistilled

ORD record

ord-8557e94496a34f3aa0c32a04b3b65fde

Source dataset

uspto-grants-1983_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04388104