Ethyl 2-furoate → 2-Cyclohexyl-3-furan-2-yl-3-oxo-propionic acid methyl ester

HRID 460733

反応式

HRID 460733 の反応式
[H-].[Na+].[CH:3]1([CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[O:14]1[CH:18]=[CH:17][CH:16]=[C:15]1[C:19](OCC)=[O:20]>>[CH3:13][O:12][C:10](=[O:11])[CH:9]([CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1)[C:19]([C:15]1[O:14][CH:18]=[CH:17][CH:16]=1)=[O:20]

参加物

4

反応物 3

HCID 11980Ethyl 2-furoateHCID 24758Sodium hydrideHCID 139743Cyclohexaneacetic acid, methyl ester

生成物 1

HCID 588250272-Cyclohexyl-3-furan-2-yl-3-oxo-propionic acid methyl ester収率 76.3%

反応条件

温度
0 °C

実験手順

To an ice cold suspension of 0.92 g (23 mmol) of sodium hydride (NaH 60% dispersion in mineral oil) (previously washed with hexane and dried under vacuum) in 25 mL of 1,2-dimethoxyethane (DME) was added 0.9 g (5.76 mmol) of methyl cyclohexylacetate, and the resulting mixture was stirred at 0° C. for 20 min. Then 1.2 g (8.56 mmol) of ethyl 2-furoate was added, and the reaction mixture was heated at reflux overnight. The mixture was then cooled to 0° C., quenched by the addition of 1 M HCl solution to pH=3, and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over sodium sulfate and concentrated to give a brown oil which was chromatographed on silica gel (Biotage; 10% hexane in dichloromethane) to afford 1.1 g (76% yield) of desired 2-cyclohexyl-3-furan-2-yl-3-oxo-propionic acid methyl ester as indicated by 1H NMR.

後処理

  1. washpreviously washed with hexane
  2. dry with materialdried under vacuum) in 25 mL of 1,2-dimethoxyethane (DME)
  3. temperaturethe reaction mixture was heated
  4. temperatureat reflux overnight
  5. temperatureThe mixture was then cooled to 0° C.
  6. customquenched by the addition of 1 M HCl solution to pH=3
  7. extractionextracted with ethyl acetate
  8. washThe combined organic extracts were washed with brine
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated
  11. customto give a brown oil which
  12. customwas chromatographed on silica gel (Biotage; 10% hexane in dichloromethane)

出典と根拠

ORDレコード
ord-d8ea24fa5f7a40b2b3fd76d2cb33b281
出典データセット
uspto-grants-2007_03
特許番号
US07196111B2

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