Water → HCID 22915511, 화합물

HRID 1377919노트

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HRID 1377919 반응식
[C:1]([O:5][C:6](=[O:31])[CH2:7][CH2:8][CH:9](C(OCC)=O)[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][CH:19]=2)=[CH:14][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].[OH-:32].[Li+].O.C[CH:36]([OH:38])C>>[C:1]([O:5][C:6](=[O:31])[CH2:7][CH:8]([C:36]([OH:38])=[O:32])[CH2:9][CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]2[CH:19]=[CH:20][C:21]([C:24]#[N:25])=[CH:22][CH:23]=2)=[CH:16][CH:17]=1)([CH3:2])([CH3:3])[CH3:4]

참가 물질

5

반응물 4

HCID 962WaterHCID 3776IsopropanolHCID 3939Lithium HydroxideHCID 54269919HCID 54269919, 화합물

생성물 1

HCID 22915511HCID 22915511, 화합물

실험 절차

To a solution in 2-propanol (30 mL) of 4-carboethoxy-5-[4-(4-cyanophenyl)phenoxy]pentanoic acid tert-butyl ester (0.9 g), prepared in step 1, was added aqueous 1M lithium hydroxide (8.6 mmol) and water (5 mL) to form a clear solution, and the reaction mixture was stirred for 3 hours. The reaction mixture was quenched with saturated aqueous NH4Cl and extracted twice with ethyl ether and once with ethyl acetate. The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. Chromatography on silica gel (4% methanol-dichloromethane) provided 3-carboxy-5-[4-(4-cyanophenyl)phenoxy]pentanoic acid tert-butyl ester (0.62 g).

후처리

  1. customto form a clear solution
  2. customThe reaction mixture was quenched with saturated aqueous NH4Cl
  3. extractionextracted twice with ethyl ether and once with ethyl acetate
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-4fb825ecaca14411928a4b5072c7579c
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05665777

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