Diethyl Ether → tert-Butyl(4-fluoro-3,5-diisopropoxybenzyloxy)dimethylsilane
Reaction equation
Br[CH:2]([CH3:4])[CH3:3].[C:5]([O-])([O-])=O.[K+].[K+].[Si]([O:18][C:19]1[C:20]([F:35])=[C:21]([OH:34])[CH:22]=[C:23]([CH2:25][O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])[CH:24]=1)(C(C)(C)C)(C)C.C(O[CH2:39][CH3:40])C>CN(C=O)C>[C:30]([Si:27]([O:26][CH2:25][C:23]1[CH:22]=[C:21]([O:34][CH:2]([CH3:4])[CH3:3])[C:20]([F:35])=[C:19]([O:18][CH:39]([CH3:40])[CH3:5])[CH:24]=1)([CH3:28])[CH3:29])([CH3:31])([CH3:32])[CH3:33]Participants
6
Conditions
- Temperature
- 60 °C
Procedure
2-Bromopropane (0.90 mL, 9.5 mmol) and K2CO3 (1.49 g, 10.8 mmol) were added to a stirred solution of 3-(tert-butyldimethylsilyloxy)-5-((tert-butyldimethylsilyloxy)methyl)-2-fluorophenol (5) (2.08 g, 4.30 mmol) in DMF (3 mL) and the mixture was stirred at 60° C. for 2 h. The reaction mixture was allowed to cool to RT and diluted with diethyl ether (50 mL). The organic solution was washed with brine (3×50 mL), dried over MgSO4, filtered and the solvent was removed in vacuo to afford tert-butyl(4-fluoro-3,5-diisopropoxybenzyloxy)dimethylsilane (6) (0.6 g, 31%). This material was used in the subsequent reaction step without purification.
Workup
- temperatureto cool to RT
- washThe organic solution was washed with brine (3×50 mL)
- dry with materialdried over MgSO4
- filtrationfiltered
- customthe solvent was removed in vacuo
Sources & evidence
- ORD record
- ord-8f6d7b307ed64b84a8bce5da9b5510fc
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09447028B2
Reaction notes
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