Isobutylene oxide → 2-Methyl-1-[(8-methyl-1,4-dioxaspiro[4.5]dec-8-yl)oxy]propan-2-ol
Reaction equation
[CH3:1][C:2]1([OH:12])[CH2:11][CH2:10][C:5]2([O:9][CH2:8][CH2:7][O:6]2)[CH2:4][CH2:3]1.[H-].[Na+].[CH3:15][C:16]1([O:19][CH2:18]1)[CH3:17]>CN(C)C=O.O>[CH3:15][C:16]([OH:19])([CH3:18])[CH2:17][O:12][C:2]1([CH3:1])[CH2:11][CH2:10][C:5]2([O:6][CH2:7][CH2:8][O:9]2)[CH2:4][CH2:3]1Participants
Procedure
To a solution of 8-methyl-1,4-dioxaspiro[4.5]decan-8-ol (4.01 g) in N,N-dimethylformamide (20 mL) was added 60% sodium hydride in oil (960 mg) under ice-cooling, and the mixture was stirred at room temperature for 1 hr. To this mixture was added isobutylene oxide (2.52 g), and the mixture was stirred at 90° C. for 15 hr. The reaction mixture was cooled to room temperature, and diluted with water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography [eluent: hexane/ethyl acetate=80/20→65/35 (volume ratio)] to give the title compound as a colorless oil (1.81 g, 32%).
Workup
- temperaturecooling
- stirringthe mixture was stirred at 90° C. for 15 hr
- temperatureThe reaction mixture was cooled to room temperature
- extractionthe mixture was extracted with ethyl acetate
- washThe extract was washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- customThe solvent was evaporated under reduced pressure
- customthe residue was purified by silica gel chromatography [eluent: hexane/ethyl acetate=80/20→65/35 (volume ratio)]
Sources & evidence
- ORD record
- ord-cf40f9ad8ab543cd84437454bbb2d681
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08592431B2
Reaction notes
Loading…