Diethyl Ether → 1-Cyano-2-[(3-methoxyphenyl)methyl]cyclohexane

HRID 377296노트

반응식

HRID 377296 반응식
CC(C)([O-])C.[K+].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH2:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][C:17]2=O)[CH:12]=[CH:13][CH:14]=1.C1(C)C=CC(S([CH2:32][N+:33]#[C-])(=O)=O)=CC=1.C(OCC)C>C(O)(C)(C)C.COCCOC.COCCOC.O>[C:32]([CH:17]1[CH2:18][CH2:19][CH2:20][CH2:21][CH:16]1[CH2:15][C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([O:8][CH3:7])[CH:10]=1)#[N:33]

참가 물질

8

반응물 4

HCID 3283Diethyl EtherHCID 161915Tosylmethyl isocyanideHCID 148680162-(3-Methoxy-benzyl)-cyclohexanoneHCID 23665647Potassium tert-butoxide

생성물 1

HCID 193584921-Cyano-2-[(3-methoxyphenyl)methyl]cyclohexane수율 86.6%

시약·촉매·용매 3

HCID 962Water용매HCID 80711,2-Dimethoxyethane용매HCID 86596206tert butanol DME용매

실험 절차

A solution of potassium tert-butoxide (4.10 g) in tert-butanol-1,2-dimethoxyethane (1:1, 38 ml) was added dropwise to a stirred solution of 2-[(3-methoxyphenyl)-methyl]cyclohexanone (4.10 g) and (p-tolylsulfonyl)methyl isocyanide (4.10 g) in 1,2-dimethoxyethane under ice cooling over 30 minutes. The resulting mixture was stirred at the same temperature for 1 hour and at room temperature for 2 hours and 30 minutes, and then a mixture of diethyl ether and water was added thereto. The organic layer was separated, washed with water and brine, dried over magnesium sulfate, and evaporated in vacuo. The oily residue was chromatographed over silica gel using n-hexane--ethyl acetate as an eluent to afford 1-cyano-2-[(3-methoxyphenyl)methyl]cyclohexane (3.73 g) as an oil.

후처리

  1. additionwas added
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe oily residue was chromatographed over silica gel

출처 및 근거

ORD 기록
ord-8fc6da633c114998b50b57fe3fdebd3a
출처 데이터셋
uspto-grants-2000_02
특허 번호
US06025375

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