Ethyl 3-(4,6-di-t-butyl-2-methyl-5-trimethylsilyloxy-2,3-dihydrobenzofuran-2-yl)-2-propenoate → Ethyl 3-(4,6-di-t-butyl-2-methyl-5-trimethylsilyloxy-2,3-dihydrobenzofuran-2-yl)propanoate
Reaction equation
[C:1]([C:5]1[C:10]2[CH2:11][C:12]([CH:15]=[CH:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])([CH3:14])[O:13][C:9]=2[CH:8]=[C:7]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:6]=1[O:26][Si:27]([CH3:30])([CH3:29])[CH3:28])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[C].[Pd]>[C:1]([C:5]1[C:10]2[CH2:11][C:12]([CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])([CH3:14])[O:13][C:9]=2[CH:8]=[C:7]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:6]=1[O:26][Si:27]([CH3:30])([CH3:29])[CH3:28])([CH3:2])([CH3:3])[CH3:4]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 0.27 g of ethyl 3-(4,6-di-t-butyl-2-methyl-5-trimethylsilyloxy-2,3-dihydrobenzofuran-2-yl)-2-propenoate synthesized in Example 75-1) in 20 ml of ethanol was added a catalytic amount of 10% palladium-carbon, and the mixture was stirred for 48 hours under a hydrogen atmosphere. After the catalyst was filtered off, the filtrate was concentrated and the residue was purified on a short column of silica gel eluting with n-hexane containing 9% ethyl acetate to give 0.27 g of ethyl 3-(4,6-di-t-butyl-2-methyl-5-trimethylsilyloxy-2,3-dihydrobenzofuran-2-yl)propanoate as a colorless viscous liquid.
Workup
- filtrationAfter the catalyst was filtered off
- concentrationthe filtrate was concentrated
- customthe residue was purified on a short column of silica gel eluting with n-hexane containing 9% ethyl acetate
Sources & evidence
- ORD record
- ord-4c0e75a4ddbd4f41962e718384bbf934
- Source dataset
- uspto-grants-2000_10
- Patent number
- US06133279
Reaction notes
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