Imidazole → Diethyl 3-(tert-butyldiphenylsiloxy)glutarate

HRID 2249286

Reaction equation

HRID 2249286 reaction equation
[OH:1][CH:2]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[Si:15](Cl)([C:28]([CH3:31])([CH3:30])[CH3:29])([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.N1C=CN=C1.O>CN(C)C=O.ClCCl.CCCCCC>[O:1]([CH:2]([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[Si:15]([C:28]([CH3:31])([CH3:30])[CH3:29])([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 94078tert-ButyldiphenylchlorosilaneHCID 96259Diethyl 3-hydroxyglutarate

Product 1

HCID 19825423Diethyl 3-(tert-butyldiphenylsiloxy)glutarateYield 96.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21226440Methylenechloride HexaneSolvent

Procedure

To a solution of 1.22 g (5.97 mmol) of diethyl 3-hydroxyglutarate in dry dimethylformamide (30 ml) were added 1.95 g (7.09 mmol) of tert-butyldiphenylsilyl chloride and 1.41 g (20.7 mmol) of imidazole in an atmosphere of argon, and the mixture was allowed to react at room temperature for 10 hours. To the solution was added water followed by extraction with benzene. The organic layer was washed with water and concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography for separation and purification. From the eluate with dichloromethane-hexane (1:1) was afforded 2.54 g (5.75 mmol) of diethyl 3-(tert-butyldiphenylsiloxy)glutarate.

Workup

  1. customto react at room temperature for 10 hours
  2. extractionfollowed by extraction with benzene
  3. washThe organic layer was washed with water
  4. concentrationconcentrated under reduced pressure
  5. customThe residue thus obtained
  6. customwas subjected to silica gel column chromatography for separation and purification

Sources & evidence

ORD record
ord-b137e4dd1add486fa79b10bc2fba854c
Source dataset
uspto-grants-1991_08
Patent number
US05043142

Linked notes

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