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

HRID 377296ノート

反応式

HRID 377296 の反応式
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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒HCID 86596206tert butanol DME溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8fc6da633c114998b50b57fe3fdebd3a
出典データセット
uspto-grants-2000_02
特許番号
US06025375

反応ノート

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