Isobutylene oxide → 1-(1,4-Dioxaspiro[4.5]dec-8-yloxy)-2-methylpropan-2-ol

HRID 2048501Notes

Reaction equation

HRID 2048501 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([OH:11])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[H-].[Na+].[CH3:14][C:15]1([O:18][CH2:17]1)[CH3:16]>CN(C)C=O.O>[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([O:11][CH2:14][C:15]([CH3:17])([OH:18])[CH3:16])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 11208Isobutylene oxideHCID 24758Sodium hydrideHCID 5673521,4-Dioxaspiro(4.5)decan-8-ol

Product 1

HCID 670091781-(1,4-Dioxaspiro[4.5]dec-8-yloxy)-2-methylpropan-2-olYield 78.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1,4-dioxaspiro[4.5]decan-8-ol (4.90 g) in N,N-dimethylformamide (20 mL) was added 60% sodium hydride in oil (1.24 g) under ice-cooling, and the mixture was stirred at room temperature for 1 hr. Isobutylene oxide (2.52 g) was added to this mixture, 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=90/10→70/30 (volume ratio)] to give the title compound as a colorless oil (5.59 g, 78%).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at 90° C. for 15 hr
  3. temperatureThe reaction mixture was cooled to room temperature
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel chromatography [eluent: hexane/ethyl acetate=90/10→70/30 (volume ratio)]

Sources & evidence

ORD record
ord-da7e47e8e218421a8683dff024214166
Source dataset
uspto-grants-2013_11
Patent number
US08592431B2

Reaction notes

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