Ethyl Acetate → HCID 10660119, compound

HRID 446523Notes

Reaction equation

HRID 446523 reaction equation
[OH:1][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].Br[CH2:11][CH2:12][CH2:13][O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16].C(OCC)(=O)C>CN(C)C=O>[Si:15]([O:14][CH2:13][CH2:12][CH2:11][O:1][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])([C:18]([CH3:19])([CH3:20])[CH3:21])([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 12184Ethyl GlycolateHCID 24758Sodium hydrideHCID 607486(3-Bromopropoxy)(tert-butyl)dimethylsilane

Product 1

HCID 10660119HCID 10660119, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl hydroxyacetate (600 mg, 5.76 mmol) was dissolved in N,N-dimethylformamide (6 mL), sodium hydride (55%; 277 mg, 0.447 mmol) was added under ice cooling, and then the mixture was stirred at room temperature for 30 minutes. (3-Bromopropoxy)(tert-butyl)dimethylsilane (1.46 mL, 6.34 mmol) was added, and the mixture was stirred at room temperature for 6.5 hours. Ethyl acetate was added to the reaction mixture, and the organic layer was washed with water (×3) and saturated sodium chloride solution. The organic layer was dried with anhydrous sodium sulfate, then the solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1, v/v) to give the title compound (842 mg; yield, 53%) as a colorless oily substance.

Workup

  1. stirringthe mixture was stirred at room temperature for 6.5 hours
  2. washthe organic layer was washed with water (×3) and saturated sodium chloride solution
  3. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customthe resulting residue was purified by silica gel column chromatography (hexane

Sources & evidence

ORD record
ord-39cc4c2ceb604b6db5e7c5ad54321d06
Source dataset
uspto-grants-2013_07
Patent number
US08476253B2

Reaction notes

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