Potassium Carbonate → Nonanoic acid, 9-hydroxy-, methyl ester

HRID 2404930Notes

Reaction equation

HRID 2404930 reaction equation
[CH3:1][O:2][C:3](=[O:14])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11](O)=[O:12].B.CSC.C([O-])([O-])=O.[K+].[K+]>C1COCC1>[CH3:1][O:2][C:3](=[O:14])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][OH:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 75009Monomethyl azelateHCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 292983Nonanoic acid, 9-hydroxy-, methyl esterYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of nonanedioic acid monomethyl ester (4.80 g, 20 mmol) in THF (20 mL) at −20° C. was added a solution of borane-dimethylsulfide in THF (2.0 M, 10 mL) over 10 min. The resulting mixture was stirred for an additional 10 min, and then allowed to stir at room temperature overnight. Aqueous K2CO3 solution was added, and the product was extracted with ethyl ether (3×). The crude product was purified by flash column chromatography (hexane/EtOAc:2/1) to yield 9-hydroxy-nonanoic acid methyl ester 4-B (2.0 g, 55%).

Workup

  1. stirringto stir at room temperature overnight
  2. extractionthe product was extracted with ethyl ether (3×)
  3. customThe crude product was purified by flash column chromatography (hexane/EtOAc:2/1)

Sources & evidence

ORD record
ord-0d12c018b1664bae86e0f963c86f62c5
Source dataset
uspto-grants-2014_08
Patent number
US08802832B2

Reaction notes

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