3-Hydroxybenzaldehyde → 3-(t-Butyldimethylsilyloxy)benzaldehyde

HRID 1038642Notes

Reaction equation

HRID 1038642 reaction equation
[C:1]([Si:5]([CH3:8])([CH3:7])Cl)([CH3:4])([CH3:3])[CH3:2].[OH:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=1)[CH:13]=[O:14].N1C=CN=C1>C(Cl)(Cl)Cl>[Si:5]([O:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=1)[CH:13]=[O:14])([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 112071113-(t-Butyldimethylsilyloxy)benzaldehydeYield 54.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

t-Butyldimethylchlorosilane (26.01 g; 172.56 mmol) was added to a solution of 3-hydroxybenzaldehyde (20.7 g; 164.35 mmol) and imidazole (27.97 g; 410.9 mmol) in chloroform (300 mL) under nitrogen at 0° C. The reaction was allowed to warm to room temperature and stirred overnight. The reaction mixture was washed with water (100 mL×3) and brine (100 mL), dried over anhydrous sodium sulfate and concentrated to give crude product (29.56 g), which was purified by column chromatography on silica gel eluting with (i) pentane and (ii) 3% ethyl acetate in pentane to give 3-(t-butyl-dimethylsilanyloxy)benzaldehyde (21.0 g; 54%). 1H NMR (300 MHz, CDCl3) δ 9.93 (s, 1H), 7.45 (d, 1H, J=7.5 Hz), 7.38 (dd, 1H, J=7.5, 7.5 Hz), 7.31 (d, 1H, J=1.0 Hz), 7.09 (1H, dd, J=7.5, 1.0 Hz), 0.98 (s, 9H), 0.20 (s, 6H).

Workup

  1. washThe reaction mixture was washed with water (100 mL×3) and brine (100 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customto give crude product (29.56 g), which
  5. customwas purified by column chromatography on silica gel eluting with (i) pentane and (ii) 3% ethyl acetate in pentane

Sources & evidence

ORD record
ord-2d5b02faa3d24098ae08582765bd62ee
Source dataset
uspto-grants-2013_10
Patent number
US08551998B2

Reaction notes

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