Hydrochloric Acid → (4-{[tert-Butyl(dimethyl)silyl]oxy}-3,5-dipropylphenyl)methanol
Reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Si:7]([O:14][C:15]1[C:24]([CH2:25][CH2:26][CH3:27])=[CH:23][C:18]([C:19](OC)=[O:20])=[CH:17][C:16]=1[CH2:28][CH2:29][CH3:30])([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8].C(OCC)(=O)C.Cl>C1COCC1>[Si:7]([O:14][C:15]1[C:16]([CH2:28][CH2:29][CH3:30])=[CH:17][C:18]([CH2:19][OH:20])=[CH:23][C:24]=1[CH2:25][CH2:26][CH3:27])([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:8])[CH3:9]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Lithium aluminum hydride (9 mL of a 1M solution in THF) was added cautiously to a solution of the product of Step D at 0° C., and the reaction mixture was stirred overnight. Ethyl acetate was added to the mixture, cooled to 0° C. and treated with cold 1N HCl. After separating the organic phase, the aqueous phase was extracted with a mixture of ethyl acetate-ether-dichloromethane. The combined organic extracts were dried and concentrated. The concentrated material was purified by flash column chromatography using 20% ethyl acetate in hexane to afford 4.2 g (92%) of the title compound.
Workup
- customAfter separating the organic phase
- extractionthe aqueous phase was extracted with a mixture of ethyl acetate-ether-dichloromethane
- customThe combined organic extracts were dried
- concentrationconcentrated
- customThe concentrated material was purified by flash column chromatography
Sources & evidence
- ORD record
- ord-fba0cb9fb1b145a1af2f772c0db3ce3a
- Source dataset
- uspto-grants-1993_09
- Patent number
- US05246944
Reaction notes
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