Sodium hydride → 1-[4-(2,2-Diethoxyethoxy)phenyl]cyclopropanecarboxylic acid

HRID 468249노트

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HRID 468249 반응식
C[O:2][C:3]([C:5]1([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[CH2:7][CH2:6]1)=[O:4].[H-].[Na+].[H][H].Br[CH2:20][CH:21]([O:25][CH2:26][CH3:27])[O:22][CH2:23][CH3:24]>CN(C=O)C>[CH2:23]([O:22][CH:21]([O:25][CH2:26][CH3:27])[CH2:20][O:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2([C:3]([OH:2])=[O:4])[CH2:7][CH2:6]2)=[CH:9][CH:10]=1)[CH3:24]

참가 물질

6

반응물 4

HCID 24758Sodium hydrideHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 20770793Methyl 1-(4-hydroxyphenyl)cyclopropane-1-carboxylateHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 591292871-[4-(2,2-Diethoxyethoxy)phenyl]cyclopropanecarboxylic acid수율 40.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
160 °C

실험 절차

To a stirred solution of 1-(4-hydroxy-phenyl)-cyclopropanecarboxylic acid methyl ester (15.0 g, 84.3 mmol) in DMF (50 mL) was added sodium hydride (6.7 g, 170 mmol, 60% in mineral oil) at 0 CC. After hydrogen evolution ceased, 2-bromo-1,1-diethoxy-ethane (16.5 g, 84.3 mmol) was added dropwise to the reaction mixture. The reaction was stirred at 160° C. for 15 hours. The reaction mixture was poured onto ice (100 g) and was extracted with CH2Cl2. The combined organics were dried over Na2SO4. The solvent was evaporated under vacuum to give 1-[4-(2,2-diethoxy-ethoxy)-phenyl]-cyclopropanecarboxylic acid (10 g), which was used directly in the next step without purification.

후처리

  1. additionThe reaction mixture was poured onto ice (100 g)
  2. extractionwas extracted with CH2Cl2
  3. dry with materialThe combined organics were dried over Na2SO4
  4. customThe solvent was evaporated under vacuum

출처 및 근거

ORD 기록
ord-bae2dc94fe0c43dd9a67dd8ab512f02a
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08623905B2

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