Water → 2-[4-(3-Ethoxycarbonyl-1-propenyl)phenyl]ethyl alcohol
Reaction equation
[O:1]([CH2:9][CH2:10][C:11]1[CH:23]=[CH:22][C:14]([CH:15]=[CH:16][C:17](OCC)=O)=[CH:13][CH:12]=1)[Si](C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[OH2:42].[O:43]1[CH2:47]C[CH2:45][CH2:44]1>>[CH2:44]([O:43][C:47]([CH2:17][CH:16]=[CH:15][C:14]1[CH:13]=[CH:12][C:11]([CH2:10][CH2:9][OH:1])=[CH:23][CH:22]=1)=[O:42])[CH3:45]Participants
5
Procedure
To a solution of ethyl 4-(2-t-butyldimethylsiloxyethyl)cinnamate (1.9 g) in tetrahydrofuran (6 ml) was added dropwise tetra-n-butylammonium fluoride (1 mol/l solution in tetrahydrofuran, 6.0 ml), and the mixture was stirred at room temperature for 1.5 hours. To the reaction mixture was added water, and the mixture was extracted with diethyl ether. The extract was dried over anhydrous MgSO4. The solvent was removed under reduced pressure, and the residue was treated according to C. J. Kowalski's method described in J. Am. Chem. Soc., Vol.107, No.5, 1429-1430 (1985) to give 2-[4-(3-ethoxycarbonyl-1-propenyl)phenyl]ethyl alcohol (0.42 g) as colorless powder.
Workup
- extractionthe mixture was extracted with diethyl ether
- dry with materialThe extract was dried over anhydrous MgSO4
- customThe solvent was removed under reduced pressure
- additionthe residue was treated
Sources & evidence
- ORD record
- ord-3b30b840a5fa440195b8c1a2186b3265
- Source dataset
- uspto-grants-1997_04
- Patent number
- US05624948
Reaction notes
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