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

HRID 475704

반응식

HRID 475704 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-f0b87447097d489f8d8290601e39f4e9
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637648B1

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