Dichloromethane → (E)-7-(tert-butyldimethylsiloxy)-2-methylhept-2-enal
Reaction equation
C(N(CC)CC)C.C(Cl)Cl.[O:11]([CH2:19][CH2:20][CH2:21][CH2:22]/[CH:23]=[C:24](\[CH3:27])/[CH2:25][OH:26])[Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]>CS(C)=O>[O:11]([CH2:19][CH2:20][CH2:21][CH2:22]/[CH:23]=[C:24](\[CH3:27])/[CH:25]=[O:26])[Si:12]([C:15]([CH3:17])([CH3:18])[CH3:16])([CH3:14])[CH3:13]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
After the addition of triethylamine (36.5 ml) to a methylene chloride solution (53 ml) of Alcohol 5 (13.6 g) and cooling to 0° C., a dimethylsulfoxide solution (53 ml) of SO3-pyridine (25 g) is added thereto at 0° C. and the whole is stirred for 1.5 hours. After stirring, the resultant solution is quenched using a buffer solution (5 ml) and the organic compound is extracted three times with ethyl acetate, followed by the wash of the organic layer in a saturated saline solution and drying over anhydrous sodium sulfate. After anhydrous sodium sulfate is filtered and the solvent is distilled off under reduced pressure, the residue is separated and purified by column chromatography to produce Aldehyde 6 (12.8 g) of 94% in yield.
Workup
- stirringAfter stirring
- customthe resultant solution is quenched
- extractionthe organic compound is extracted three times with ethyl acetate
- washwash of the organic layer in a saturated saline solution
- dry with materialdrying over anhydrous sodium sulfate
- filtrationAfter anhydrous sodium sulfate is filtered
- distillationthe solvent is distilled off under reduced pressure
- customthe residue is separated
- custompurified by column chromatography
Sources & evidence
- ORD record
- ord-aebe91789a304cd5b734e42dc19d992c
- Source dataset
- uspto-grants-2009_11
- Patent number
- US07612213B2
Reaction notes
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