4-Hydroxybenzaldehyde → 4-(2-(Tert-butyldimethylsilyloxy)ethoxy)benzaldehyde
Reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][CH2:18][O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21].O>CC#N>[O:19]([CH2:18][CH2:17][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)[Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]Participants
6
Procedure
To a stirred suspension of 4-hydroxybenzaldehyde (0.500 g, 4.012 mmol) and anhydrous potassium carbonate (0.833 g, 6.019 mmol) in dry MeCN (15 ml) at room temperature was added 2-bromo-1-tert-butyldimethylsiloxyethane (83%, 1.730 g, 6.019 mmol), and the reaction mixture was heated under reflux for 20.5 h. Water (25 ml) was added and the reaction mixture was extracted with Et2O (4×25 ml). The combined organic extracts were washed with brine (50 ml), dried (Na2SO4), and the solvent was removed under reduced pressure to give a pale yellow oil that was purified by flash chromatography (3:1 Hexane/Et2O) to give the title compound (0.895 g, 79.5%) as a colourless oil.
Workup
- temperaturethe reaction mixture was heated
- temperatureunder reflux for 20.5 h
- extractionthe reaction mixture was extracted with Et2O (4×25 ml)
- washThe combined organic extracts were washed with brine (50 ml)
- dry with materialdried (Na2SO4)
- customthe solvent was removed under reduced pressure
- customto give a pale yellow oil that
- customwas purified by flash chromatography (3:1 Hexane/Et2O)
Sources & evidence
- ORD record
- ord-4ebaf48e08e24b8d90213a9d59741425
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08895313B2
Reaction notes
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