Sodium Chloride → Trans-3-[2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]5-cyanocyclohexanone

HRID 1758154노트

반응식

HRID 1758154 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([C:15]([CH3:23])([CH3:22])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:12]=[CH:11][C:10]=1[CH:24]1[CH2:29][C:28](=[O:30])[CH:27]=[CH:26][CH2:25]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OCC)(=O)C.[C-:37]#[N:38].[K+].[Cl-].[Na+]>CCOCC.C(O)C.O>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([C:15]([CH3:22])([CH3:23])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:12]=[CH:11][C:10]=1[C@H:24]1[CH2:25][C@H:26]([C:37]#[N:38])[CH2:27][C:28](=[O:30])[CH2:29]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

8

반응물 4

HCID 5234Sodium ChlorideHCID 8857Ethyl AcetateHCID 9032Potassium Cyanide2회HCID 127882935-(2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]-2-cyclohexen-1-one

생성물 1

HCID 13105260Trans-3-[2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]5-cyanocyclohexanone수율 71%

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매HCID 3283Diethyl Ether용매

실험 절차

To a refluxing solution of 3.99 g. (9.87 mmole) of 5-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-2-cyclohexen-1-one in 6.65 ml. of ethyl acetate was added a hot solution of 800 mg. (11.9 mmole) of potassium cyanide in 2 ml. water and 2.3 ml. ethanol. The reaction was refluxed 2 hours and then another 2.74 mmole of potassium cyanide added. The reaction was refluxed one hour longer and then cooled and added to 400 ml. saturated sodium chloride-400 ml. ether. The ether extract was dried over magnesium sulfate and evaporated to yield an oil. The crude oil was purified via column chromatography on 160 g. of silica gel eluted with 10% acetone-hexane to yield 3.02 g. (71%) of the title compound.

후처리

  1. temperatureThe reaction was refluxed 2 hours
  2. temperatureThe reaction was refluxed one hour longer
  3. temperaturecooled
  4. additionadded to 400 ml
  5. extractionThe ether extract
  6. dry with materialwas dried over magnesium sulfate
  7. customevaporated
  8. customto yield an oil
  9. customThe crude oil was purified via column chromatography on 160 g
  10. washof silica gel eluted with 10% acetone-hexane
  11. customto yield 3.02 g

출처 및 근거

ORD 기록
ord-44d28fe791964f57af8467544c5d209a
출처 데이터셋
uspto-grants-1983_02
특허 번호
US04371720

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