Sodium hydride → Methyl 2-(3-bromobenzyloxy)-2-methylpropionate

HRID 31552

Reaction equation

HRID 31552 reaction equation
[OH:1][C:2]([CH3:8])([CH3:7])[C:3]([O:5][CH3:6])=[O:4].[H-].[Na+].[Br:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH2:15]Br.[Cl-].[NH4+]>C1COCC1>[Br:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH2:15][O:1][C:2]([CH3:8])([CH3:7])[C:3]([O:5][CH3:6])=[O:4]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 699793-Bromobenzyl bromideHCID 75024Methyl alpha-hydroxyisobutyrate

Product 1

HCID 23116986Methyl 2-(3-bromobenzyloxy)-2-methylpropionateYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-hydroxyisobutyrate (1 g, 4.0 mmol) in THF (20 ml) was added sodium hydride (60% in parafin liquid) (115 mg, 4.8 mmol) at 0° C., and the mixture was stirred at room temperature for 15 minutes. To the mixture was added 3-bromobenzyl bromide (567 mg, 4.8 mmol), and the mixture was stirred at 50° C. for 12 hours. To the reaction solution was added a saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to give the title compound (520 mg, 52%).

Workup

  1. stirringthe mixture was stirred at 50° C. for 12 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-2be8a39179534e24bc2aec73a48197a3
Source dataset
uspto-grants-2008_09
Patent number
US07425642B2

Linked notes

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