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

HRID 382005Notes

Reaction equation

HRID 382005 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-4e6d7e8ac07941c4b62e98f4091d403a
Source dataset
uspto-grants-2001_10
Patent number
US06307047B1

Reaction notes

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