N,N-Dimethylformamide--water (1/1) → 3-Cyclopropyl-3-(4-hydroxyphenyl)propanoic acid

HRID 2101781Notes

Reaction equation

HRID 2101781 reaction equation
[CH:1]1([CH:4]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)[CH:5]2C(=O)OC(C)(C)[O:7][C:6]2=[O:14])[CH2:3][CH2:2]1.CN(C=O)C.O>CCOC(C)=O>[CH:1]1([CH:4]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)[CH2:5][C:6]([OH:14])=[O:7])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 21962138N,N-Dimethylformamide--water (1/1)HCID 576724845-(Cyclopropyl(4-hydroxyphenyl)methyl)-2,2-dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 576725253-Cyclopropyl-3-(4-hydroxyphenyl)propanoic acid

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 21.2 in 10:1 DMF/water (48 mL) was stirred overnight at 90° C. The mixture was cooled to room temperature, diluted with EtOAc, washed with 1 N HCl and brine, dried (MgSO4), and concentrated to afford 21.3. The crude product was used without further purification.

Workup

  1. washwashed with 1 N HCl and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-c9b43c88a22a4f5db78d5fad178d2fde
Source dataset
uspto-grants-2009_08
Patent number
US07572934B2

Reaction notes

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