Imidazole → HCID 10936741, compound

HRID 1738902Notes

Reaction equation

HRID 1738902 reaction equation
[OH:1][CH2:2][C:3]([CH3:7])([CH3:6])[CH:4]=[O:5].[Si:8](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.N1C=CN=C1.O>CN(C)C=O>[Si:8]([O:5][CH2:4][C:3]([CH3:7])([CH3:6])[CH:2]=[O:1])([C:21]([CH3:24])([CH3:23])[CH3:22])([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 116993-Hydroxy-2,2-dimethylpropionaldehydeHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 10936741HCID 10936741, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Hydroxy-2,2-dimethylpropanal (5.1 g, 50 mmol) and tert-butyl-diphenylsilyl chloride (15.10 g, 55 mmol) were dissolved in dimethylformamide (50 ml). Imidazole (3.74 g, 55 mmol) was added in one portion. After stirring for 18 hours the mixture was hydrolyzed with water and extracted several times with ether. The combined organic layers were dried with MgSO4. The filtrate was concentrated under reduced pressure, and the residue was purified by flash chromatography (hexane/ethyl acetate 15:1) to give the title compound (9.55 g, 56%) as a colorless oil.

Workup

  1. extractionextracted several times with ether
  2. dry with materialThe combined organic layers were dried with MgSO4
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was purified by flash chromatography (hexane/ethyl acetate 15:1)

Sources & evidence

ORD record
ord-8375ecbc3d13404bb5de7533010322af
Source dataset
uspto-grants-1999_10
Patent number
US05965553

Reaction notes

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