Water → HCID 19835580, compound
Reaction equation
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[CH3:9][C:10]([CH3:22])([CH3:21])[C:11](=[O:20])[CH2:12][O:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][O:15]1.O>CS(C)=O>[C:10]([C:11]1([CH2:12][O:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][O:15]2)[CH2:4][O:20]1)([CH3:22])([CH3:21])[CH3:9]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 10 °C
Procedure
880 ml of absolute dimethylsulphoxide are added dropwise to a mixture of 38.2 g (1.27 mols) of sodium hydride (80% strength) and 271.5 g (1.23 mols) tri-methyl-oxosulphonium iodide at 10° C. under a nitrogen atmosphere, with stirring. The mixture is subsequently stirred for a further hour at room temperature and is then cooled to 10° C., and a solution of 219 g (1.1 mols) of 3,3-dimethyl-1-(tetrahydro-2H-pyran-2-yloxy)-butan-2-one in 250 ml of absolute dimethylsulphoxide is added dropwise at this temperature. The reaction mixture is stirred at room temperature for 48 hours and then poured into water. The mixture is extracted with ethyl acetate and the combined organic phases are washed with water, dried over sodium sulphate and concentrated by stripping off the diluent under reduced pressure. 219.4 g (94% of theory) of 2-tert.-butyl-2-(tetrahydro-2H-pyran-2-yloxymethyl) oxirane are obtained in this manner.
Workup
- stirringThe mixture is subsequently stirred for a further hour at room temperature
- stirringThe reaction mixture is stirred at room temperature for 48 hours
- extractionThe mixture is extracted with ethyl acetate
- washthe combined organic phases are washed with water
- dry with materialdried over sodium sulphate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-84672369a8fa4b9da0526bf206ad6859
- Source dataset
- uspto-grants-1989_12
- Patent number
- US04888048
Reaction notes
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