Imidazole → Benzaldehyde, 2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-

HRID 863781Notes

Reaction equation

HRID 863781 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].N1C=CN=C1.[Si:15](Cl)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]>CN(C=O)C>[Si:15]([O:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5])([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 6998SalicylaldehydeHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 10900635Benzaldehyde, 2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-Yield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-hydroxybenzaldehyde (500 mg, 0.44 ml, 4.09 mmol), imidazole (685 mg) and tert-butyldimethylsilyl chloride (680 mg) in DMF is stirred for 24 hours at room temperature. After hydrolysis and customary extraction, chromatography gives 28 (890 mg, 93%).

Workup

  1. customAfter hydrolysis and customary extraction, chromatography

Sources & evidence

ORD record
ord-aa289e50a0f44146b6049ebd2c54f19c
Source dataset
uspto-grants-1996_10
Patent number
US05561119

Reaction notes

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