Sodium hydride → HCID 45381710, 화합물

HRID 1402883노트

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HRID 1402883 반응식
[C:1]([CH2:3]P(=O)(OCC)OCC)#[N:2].[H-].[Na+].[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=O)=[CH:17][CH:16]=1>COCCOC>[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:21][CH2:22]/[C:23](/[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[CH:3]/[C:1]#[N:2])=[CH:19][CH:20]=1.[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:21][CH2:22]/[C:23](/[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[CH:3]\[C:1]#[N:2])=[CH:19][CH:20]=1

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 2447713-(4-chlorophenyl)-1-phenylpropan-1-one

생성물 2

HCID 45381710HCID 45381710, 화합물HCID 66759042HCID 66759042, 화합물

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

실험 절차

Diethyl cyanomethylphosphonate (0.8 ml) was added dropwise at rt to a slurry of sodium hydride (60% in mineral oil, 0.2 g) in anhydrous 1,2-dimethoxyethane (15 ml) under nitrogen atmosphere. The reaction mixture was stirred at rt for 1 hour and 3-(4-chlorophenyl)-1-phenylpropan-1-one (0.4 g) was added. After stirring at 80° C. for 4 h the resultant solution was poured into ice water (50 ml) and extracted with dichloromethane (3×20 ml). The combined organic layers were washed with brine (20 ml), dried (MgSO4), and evaporated in vacuo. The crude mixture was separated by flash chromatography on silica gel (hexane/ethyl acetate 10:1) to afford (Z)-5-(4-chlorophenyl)-3-phenylpent-2-enenitrile (80 mg) and (E)-5-(4-chlorophenyl)-3-phenylpent-2-enenitrile (284 mg) as colourless oils.

후처리

  1. extractionextracted with dichloromethane (3×20 ml)
  2. washThe combined organic layers were washed with brine (20 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo
  5. customThe crude mixture was separated by flash chromatography on silica gel (hexane/ethyl acetate 10:1)

출처 및 근거

ORD 기록
ord-43a056641e3e4af3abc405aefba1f619
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08912186B2

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