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Water → 4-(2-Cyclopropylethoxy)-4-(4-fluorophenyl)-1-phenylcyclohexanecarbonitrile

HRID 657513
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HRID 657513 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:22])[CH2:13][CH2:12][C:11]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)([C:14]#[N:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Br[CH2:24][CH2:25][CH:26]1[CH2:28][CH2:27]1.[H-].[Na+].O>CN(C=O)C>[CH:26]1([CH2:25][CH2:24][O:22][C:8]2([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[CH2:13][CH2:12][C:11]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)([C:14]#[N:15])[CH2:10][CH2:9]2)[CH2:28][CH2:27]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydride2회HCID 22636989(2-Bromoethyl)cyclopropane2회HCID 594425734-(4-Fluorophenyl)-4-hydroxy-1-phenylcyclohexanecarbonitrile

생성물 1

HCID 594425114-(2-Cyclopropylethoxy)-4-(4-fluorophenyl)-1-phenylcyclohexanecarbonitrile수율 47.1%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

500 mg of the compound of Example 1, 760 mg of (2-bromoethyl)cyclopropane (Chorvat et al., J. Med. Chem. 28, 194-200 (1985)) and 122 mg of sodium hydride in 20 ml of anhydrous DMF were stirred at room temperature for 19 h. 760 mg of (2-bromoethyl)cyclopropane and 122 mg of sodium hydride were then added and the mixture was stirred at room temperature for 4 days. The reaction mixture was then treated with 100 ml of water and extracted three times with 50 ml each of EA. The combined organic phases were dried over magnesium sulfate and the solvent was removed in vacuo. 290 mg of the title compound were obtained as a pale yellow oil.

후처리

  1. extractionextracted three times with 50 ml each of EA
  2. dry with materialThe combined organic phases were dried over magnesium sulfate
  3. customthe solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-f6ffb8353fe14f5891972cf2c9430c43
출처 데이터셋
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08076324B2

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