8-Methoxy-8-oxooctanoic acid → Methyl 8-hydroxyoctanoate

A solution of suberic acid monomethyl ester (1.5 g, 7.97 mmol, 1.0 equiv.) in tetrahydrofuran (THF) (32.0 mL, 0.25M) at −20° C. was treated dropwise with BH3.THF (1M solution in THF, 7.97 mL, 7.97 mmol, 1.0 equiv.). The reaction mixture was stirred overnight and was subsequently allowed to reach room temperature. The reaction mixture was then diluted with ethyl acetate (100 mL) and quenched with methanol (10 mL) and 10% HCl (10 mL). Extraction with NaHCO3 (1×20 mL), water (2×10 mL), and brine (1×10 mL), afforded methyl-8-hydroxy-octanoate (7) as a crude white solid.

1. customto reach room temperature
2. customquenched with methanol (10 mL) and 10% HCl (10 mL)
3. extractionExtraction with NaHCO3 (1×20 mL), water (2×10 mL), and brine (1×10 mL)

ORD-Eintrag

ord-01088546d2f44973907c42d83e6bd685

Quelldatensatz

uspto-grants-2004_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06699682B2