Imidazole → 4-Phenylcyclohexylmethyl iodide

HRID 2269348

反応式

HRID 2269348 の反応式
N1C=CN=C1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:25]I.[C:27]1([CH:33]2[CH2:38][CH2:37][CH:36]([CH2:39]O)[CH2:35][CH2:34]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>ClCCl.CCCCC>[C:27]1([CH:33]2[CH2:38][CH2:37][CH:36]([CH2:39][I:25])[CH2:35][CH2:34]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

参加物

7

反応物 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 3100608(4-Phenylcyclohexyl)methanol

生成物 1

HCID 183339764-Phenylcyclohexylmethyl iodide収率 89%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8003Pentane溶媒

実験手順

Imidazole (4.4 g, 0.065 mol) is added in one portion to a solution of triphenylphosphine (17.0 g, 0.065 mol) in dichloromethane (300 mL) at 25° C. After all of the solids dissolved, iodine (16.5 g, 0.065 mol) is added in four portions. The mixture is stirred for 10 min. then a solution of 4-phenylcyclohexylmethanol (10.5 g, 0.055 mol) is added dropwise and the mixture is stirred at 25° C. for 18 h. The reaction mixture is poured into pentane and the resulting solids filtered. The filtrate is concentrated in vacuo and the residue is dissolved in dichloromethane. This solution is poured into hexanes, the solids were filtered, and the filtrate is concentrated in vacuo. The residue is passed through a pad of silica gel using hexanes as eluent to afford 14.6 g (89%) of 4-phenylcyclohexylmethyl iodide as an oil.

後処理

  1. dissolutionAfter all of the solids dissolved
  2. stirringthe mixture is stirred at 25° C. for 18 h
  3. filtrationthe resulting solids filtered
  4. concentrationThe filtrate is concentrated in vacuo
  5. dissolutionthe residue is dissolved in dichloromethane
  6. additionThis solution is poured into hexanes
  7. filtrationthe solids were filtered
  8. concentrationthe filtrate is concentrated in vacuo

出典と根拠

ORDレコード
ord-41eb19a3db80431290c4337f10d21054
出典データセット
uspto-grants-2001_12
特許番号
US06329400B1

関連ノート

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