Reaction #75462

Reaction equation

suberic acid monomethyl ester

BH3.THF

→

methyl-8-hydroxy-octanoate

Solvents

ethyl acetate

tetrahydrofuran

Conditions

Workup

1. 1
   Otherto reach room temperature
2. 2
   Otherquenched with methanol (10 mL) and 10% HCl (10 mL)
3. 3
   ExtractionExtraction with NaHCO3 (1×20 mL), water (2×10 mL), and brine (1×10 mL)

Procedure

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.

Source