Dimethyl Sulfoxide → 5-((tert-Butyldimethylsilyl)oxy)pentanal
Reaction equation
CS(C)=O.C(N(CC)CC)C.[Si:12]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][OH:25])([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13].[Cl-].[NH4+]>CCCCCC.ClCCl>[Si:12]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH:24]=[O:25])([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]Participants
Conditions
- Temperature
- 0 °C
Procedure
Under a nitrogen atmosphere and at 0° C., dimethylsulfoxide (7.81 ml, 110 mmol), triethylamine (9.60 ml, 69.0 mmol), and a sulfur trioxide-pyridine complex (4.39 g, 27.6 mmol) were added to a dichloromethane solution (80 ml) of 5-(t-butyldimethylsilyloxy)pentanol (3.00 g, 13.8 mmol). The resulting mixture was stirred at 0° C. for 30 minutes and then, at room temperature for further 3 hours. After cooling to 0° C., a saturated aquoeus ammonium chloride solution was added. Dichloromethane was distilled off under reduced pressure. To the residue was added ethyl acetate. After the water layer was separated, the organic layer was washed with water and brine, dried over magnesium sulfate and then, concentrated. The residue thus obtained was subjected to chromatography on a silica gel column, and the fraction obtained from the hexane:ethyl acetate=20:1 eluate was concentrated, whereby the title compound (2.42 g, 11.2 mmol, 81%) was obtained as a colorless oil.
Workup
- waitat room temperature for further 3 hours
- temperatureAfter cooling to 0° C.
- distillationDichloromethane was distilled off under reduced pressure
- additionTo the residue was added ethyl acetate
- customAfter the water layer was separated
- washthe organic layer was washed with water and brine
- dry with materialdried over magnesium sulfate
- concentrationconcentrated
- customThe residue thus obtained
- concentrationethyl acetate=20:1 eluate was concentrated
Sources & evidence
- ORD record
- ord-c59df5db453846e3b9ec2d2902daf54c
- Source dataset
- uspto-grants-2008_07
- Patent number
- US07399775B2
Reaction notes
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