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

HRID 625730

反応式

HRID 625730 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 292983Nonanoic acid, 9-hydroxy-, methyl ester収率 55%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-4ec8fd7e5739410b8e0301f960ca1723
出典データセット
uspto-grants-2016_04
特許番号
US09308272B2

関連ノート

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