Imidazole → Butanoic acid, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, ethyl ester, (3R)-

HRID 1241867Notes

Reaction equation

HRID 1241867 reaction equation
[OH:1][C@H:2]([CH3:9])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[Si:10](Cl)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11].N1C=CN=C1>CN(C=O)C>[O:1]([C@H:2]([CH3:9])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])[Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 440030ethyl (3R)-3-hydroxybutanoate

Product 1

HCID 12914545Butanoic acid, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, ethyl ester, (3R)-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred, room temperature solution of ethyl (R)-3-hydroxybutanoate (5.00 g, 37.8 mmol) and tert-butyldimethylsilyl chloride (6.85 g, 45.5 mmol) in DMF (90 mL) was added imidazole (3.87 g, 56.9 mmol). This reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was partitioned between hexane (300 mL) and water (100 mL). The organic layer was washed with water (2×100 mL) then dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure to give the title compound.

Workup

  1. customThe reaction mixture was partitioned between hexane (300 mL) and water (100 mL)
  2. washThe organic layer was washed with water (2×100 mL)
  3. dry with materialthen dried (MgSO4)
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c0aa4ea0cfe74667a11c7f1d5c5fd2e7
Source dataset
uspto-grants-2006_10
Patent number
US07115591B2

Reaction notes

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