Imidazole → Diethyl 3-(tert-Butyldimethylsilyloxy)glutarate

HRID 1381987

Reaction equation

HRID 1381987 reaction equation
N1C=CN=C1.[Si:6](Cl)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[OH:14][CH:15]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18]>C(Cl)Cl>[CH3:10][C:9]([Si:6]([CH3:8])([CH3:7])[O:14][CH:15]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 96259Diethyl 3-hydroxyglutarate

Product 1

HCID 13327289Diethyl 3-(tert-Butyldimethylsilyloxy)glutarateYield 102%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of imidazole (40.85 g, 600 mmole) in dry CH2Cl2 (300 ml) was added dropwise a solution of t-butyldimethylsilyl chloride (45.2 g, 300 mmole) in dry CH2Cl2 (100 ml). After 15 minutes, the solution was treated dropwise over a 40 minute period with a solution of diethyl 3-hydroxyglutarate (40.8 g, 200 mmole) in CH2Cl2 (100 ml). After stirring at room temperature under argon for 18 hours, the mixture was washed with water and saturated NaCl solution, dried over Na2SO4 and evaporated. The crude product (73.04 g) was purified by chromatography on Merck silica gel (4000 ml), eluting with ethyl ether-hexane (1:9) to give title compound (~65 g, theory 63.6) as a colorless oil.

Workup

  1. washthe mixture was washed with water and saturated NaCl solution
  2. dry with materialdried over Na2SO4
  3. customevaporated
  4. customThe crude product (73.04 g) was purified by chromatography on Merck silica gel (4000 ml)
  5. washeluting with ethyl ether-hexane (1:9)

Sources & evidence

ORD record
ord-b41c852c814044aebc856d71768477a6
Source dataset
uspto-grants-1989_02
Patent number
US04804770

Linked notes

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