Water → 3-Cyclopropyl-3-(3-hydroxy-4-methoxyphenyl) propanoic acid
Reaction equation
[CH:1]1([CH:4]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([OH:23])[CH:16]=2)[CH:5]2C(=O)OC(C)(C)[O:7][C:6]2=[O:14])[CH2:3][CH2:2]1.O>CN(C=O)C>[CH:1]1([CH:4]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([OH:23])[CH:16]=2)[CH2:5][C:6]([OH:14])=[O:7])[CH2:3][CH2:2]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
To a solution of 5-(cyclopropyl(3-hydroxy-4-methoxyphenyl)methyl)-2,2-dimethyl-1,3-dioxane-4,6-dione (2.70 g) in DMF (20 mL) was added water (2.0 mL), and the mixture was stirred at 90° C. for 15 hr. The reaction mixture was cooled to room temperature, and extracted with ethyl acetate. The extract was washed with 1N hydrochloric acid and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.50 g) as a yellow oil.
Workup
- temperatureThe reaction mixture was cooled to room temperature
- extractionextracted with ethyl acetate
- washThe extract was washed with 1N hydrochloric acid and saturated brine
- dry with materialdried over anhydrous sodium sulfate
- customThe solvent was evaporated under reduced pressure
- customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-ced18cf3727149f4899de68b2d915518
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181186B2
Reaction notes
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