4-Hydroxybenzaldehyde → 4-{[tert-Butyl(dimethyl)silyl]oxy}benzaldehyde

HRID 279232Notes

Reaction equation

HRID 279232 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.N1C=CN=C1.[Si:15](Cl)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]>CN(C=O)C.CCOC(C)=O>[Si:15]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]

Participants

6

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 108791334-{[tert-Butyl(dimethyl)silyl]oxy}benzaldehydeYield 61.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

(3) 4-Hydroxybenzaldehyde (20 g, 0.164 mol) was dissolved in DMF (60 ml) and stirred at RT as imidazole (22.3 g, 0.328 mol) and tert-butyldimethylsilyl chloride (32.1 g, 0.213 mol) were added. The reaction mixture was stirred for 16 h. The solution was diluted with EtOAc, washed with water, brine, then dried (MgSO4) and concentrated in-vacuo to afford 24 g of crude 4-(tert-butyldimethylsilanyloxy)benzaldehyde.

Workup

  1. additionwere added
  2. washwashed with water, brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in-vacuo

Sources & evidence

ORD record
ord-2e1c3176a6ef478a84e23df04e7e17ae
Source dataset
uspto-grants-2002_03
Patent number
US06362217B1

Reaction notes

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