Boron trifluoride etherate → 3-(4-Benzyloxyphenyl)-2-ethoxy-2-methyl propanoic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4](=[O:26])[C:5]([O:23][CH2:24][CH3:25])([CH3:22])[CH:6]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:10][CH:9]=1)O)[CH3:2].C([SiH](CC)CC)C.B(F)(F)F.CCOCC>ClCCl>[CH2:1]([O:3][C:4](=[O:26])[C:5]([O:23][CH2:24][CH3:25])([CH3:22])[CH2:6][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:10][CH:9]=1)[CH3:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
3-(4-Benzyloxyphenyl)-2-ethoxy-3-hydroxy-2-methyl propanoic acid ethyl ester (0.358 g; 1 mmole) and triethylsilane (0.32 ml; 2 mmole) were dissolved in dry dichloromethane (4 ml) and cooled to 0° C. whereafter borontrifluoride etherate (0.284 g; 2 mmole) was added. The reaction mixture was then stirred at 0° C. for 2.5 hours and then quenched by addition of saturated sodium hydrogencarbonate (10 ml) and dichloromethane (10 ml). The aqueous layer was extracted three times with diethyl ether. The organic phases were combined and dried over sodium sulfate. Evaporation of the solvent gave 0.349 g (100% yield) of 3-(4-benzyloxyphenyl)-2-ethoxy-2-methyl propanoic acid ethyl ester.
Workup
- additionwas added
- customquenched by addition of saturated sodium hydrogencarbonate (10 ml) and dichloromethane (10 ml)
- extractionThe aqueous layer was extracted three times with diethyl ether
- dry with materialdried over sodium sulfate
- customEvaporation of the solvent
Sources & evidence
- ORD record
- ord-a256c13c20e94b9c8037bb3b9c9e359d
- Source dataset
- uspto-grants-2003_10
- Patent number
- US06630600B1
Reaction notes
Loading…