Water → 3-Ethyl-4-nitrophenylacetic acid ethyl ester

HRID 1864953노트

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HRID 1864953 반응식
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1)[CH3:2].[CH2:16]([Mg]Cl)[CH3:17].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.O>O1CCCC1>[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[C:8]([CH2:16][CH3:17])[CH:7]=1)[CH3:2]

참가 물질

6

반응물 4

HCID 962WaterHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 79517Ethyl 4-nitrophenylacetateHCID 178461633HCID 178461633, 화합물2회

생성물 1

HCID 576832433-Ethyl-4-nitrophenylacetic acid ethyl ester

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

To a solution of 4-nitrophenylacetic acid ethyl ester (1.63 g) in tetrahydrofuran (100 mL) was dropwise added 2M ethyl magnesium chloride in tetrahydrofuran (3 mL) at −15° C. under argon atmosphere, and the mixture was stirred at the same temperature for 30 minutes. After further dropwise addition of 2M ethyl magnesium chloride in tetrahydrofuran (3 mL), the mixture was stirred at −15° C. for one hour, and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (3.0 g) was added thereto at the same temperature. The mixture was stirred overnight, and water (300 mL) was added thereto, followed by extraction with chloroform (150 mL×3). The organic layers were combined, washed with saturated brine, dried over sodium sulfate and purified by column chromatography on silica gel with hexane:ethyl acetate=10:1 to give the title compound (1.09 g).

후처리

  1. customat −15° C.
  2. stirringthe mixture was stirred at −15° C. for one hour
  3. stirringThe mixture was stirred overnight
  4. extractionfollowed by extraction with chloroform (150 mL×3)
  5. washwashed with saturated brine
  6. dry with materialdried over sodium sulfate
  7. custompurified by column chromatography on silica gel with hexane

출처 및 근거

ORD 기록
ord-7b10a05eeb84425b90ab9f02349dc8a5
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07625948B2

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