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

HRID 1794056Notes

Reaction equation

HRID 1794056 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.[CH3:15][C:16]([Si:19](Cl)([CH3:21])[CH3:20])([CH3:18])[CH3:17].O>CN(C=O)C>[Si:19]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)([C:16]([CH3:18])([CH3:17])[CH3:15])([CH3:21])[CH3:20]

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 108791334-{[tert-Butyl(dimethyl)silyl]oxy}benzaldehydeYield 99.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

to a stirred solution of 4-hydroxybenzaldehyde (25.0 g, 205 mmol) in dry DMF (200 mL) was added imidazole (28.0 g, 410 mmol) and TBDMS-Cl (32.4 g, 215 mmol) under an argon atmosphere. The resulting mixture was stirred for 4 h at room temperature (rt) then water was added and the mixture was extracted with ether (2×300 mL) and dichloromethane (2×300 mL). The combined organics were dried (MgSO4), filtered and concentrated under vacuum. The crude oil was purified by filtration through silica gel (eluting with hexane-EtOAc, 95:5) to give the product as a colourless oil (48.0 g, 99%).

Workup

  1. extractionthe mixture was extracted with ether (2×300 mL) and dichloromethane (2×300 mL)
  2. dry with materialThe combined organics were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. filtrationThe crude oil was purified by filtration through silica gel (eluting with hexane-EtOAc, 95:5)

Sources & evidence

ORD record
ord-f3e8170b5c2446c393a86ceb0ec9425e
Source dataset
uspto-grants-2006_04
Patent number
US07022707B2

Reaction notes

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