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

HRID 47184

Reaction equation

HRID 47184 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10](O)=[O:11].B.C1COCC1>O1CCCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:13])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][OH:11]

Participants

5

Reactant 2

HCID 5541918-Methoxy-8-oxooctanoic acidHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 554055Methyl 8-hydroxyoctanoate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

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.

Workup

  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)

Sources & evidence

ORD record
ord-01088546d2f44973907c42d83e6bd685
Source dataset
uspto-grants-2004_03
Patent number
US06699682B2

Linked notes

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