Imidazole → 4-Phenylcyclohexylmethyl iodide

HRID 2269348

반응식

HRID 2269348 반응식
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

참가 물질

7

반응물 4

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

생성물 1

HCID 183339764-Phenylcyclohexylmethyl iodide수율 89%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8003Pentane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-41eb19a3db80431290c4337f10d21054
출처 데이터셋
uspto-grants-2001_12
특허 번호
US06329400B1

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