Water → HCID 22915511, compound

HRID 1377919Notes

Reaction equation

HRID 1377919 reaction equation
[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]

Participants

5

Reactant 4

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

Product 1

HCID 22915511HCID 22915511, compound

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-4fb825ecaca14411928a4b5072c7579c
Source dataset
uspto-grants-1997_09
Patent number
US05665777

Reaction notes

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