Acetic Acid → 2-((1R,3R,4S)-1-methyl-4-isopropylcyclohex-3-yloxy)propionitrile

HRID 248850

반응식

HRID 248850 반응식
[H-].[Na+].[CH3:3][C@H:4]1[CH2:9][C@@H:8]([OH:10])[C@H:7]([CH:11]([CH3:13])[CH3:12])[CH2:6][CH2:5]1.[C:14](#[N:17])[CH:15]=[CH2:16].C(O)(=O)C>ClCCl.O>[CH3:3][C@@H:4]1[CH2:5][CH2:6][C@@H:7]([CH:11]([CH3:13])[CH3:12])[C@H:8]([O:10][CH:15]([CH3:16])[C:14]#[N:17])[CH2:9]1

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 7855AcrylonitrileHCID 16666(-)-MentholHCID 24758Sodium hydride

생성물 1

HCID 572047402-((1R,3R,4S)-1-methyl-4-isopropylcyclohex-3-yloxy)propionitrile

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

실험 절차

1 g of a sodium hydride suspension (50% strength) in paraffin oil was added at a temperature of 0° C. to a solution of 30 g of L-menthol in 300 ml of dichloromethane. A solution of 12.5 ml acrylonitrile in 50 ml dichloromethane was slowly added dropwise, and the reaction mixture was then stirred at room temperature for a further 5 hours. The reaction mixture was worked up by cautiously adding 10 ml of glacial acetic acid, followed by 200 ml of water, and then extracting the mixture with dichloromethane. The dichloromethane extract was dried over sodium sulfate, filtered and concentrated. After chromatographic purification of the residue on silica gel using n-hexane/dichloromethane as the eluent, 25.03 g of crude 2-((1R,3R,4S)-1-methyl-4-isopropylcyclohex-3-yloxy)propionitrile were obtained and used for the next reaction step without further purification.

후처리

  1. extractionextracting the mixture with dichloromethane
  2. extractionThe dichloromethane extract
  3. dry with materialwas dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customAfter chromatographic purification of the residue on silica gel

출처 및 근거

ORD 기록
ord-339e1ff250f641c3b64602c0196a7803
출처 데이터셋
uspto-grants-1993_05
특허 번호
US05212173

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