Imidazole → 4-[(Tert-butyldimethylsilyl)oxy]-2-chlorobenzaldehyde

HRID 1985992Notes

Reaction equation

HRID 1985992 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[Si:11](Cl)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].N1C=CN=C1>CN(C)C=O>[Si:11]([O:10][C:8]1[CH:7]=[CH:6][C:3]([CH:4]=[O:5])=[C:2]([Cl:1])[CH:9]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 1853632-Chloro-4-hydroxybenzaldehyde

Product 1

HCID 589074694-[(Tert-butyldimethylsilyl)oxy]-2-chlorobenzaldehydeYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-chloro-4-hydroxybenzaldehyde (5.0 g, 32 mmol), tert-butyl(dimethyl)silyl chloride (5.3 g, 35 mmol), imidazole (2.9 g, 45 mmol) and N,N-dimethylaminopyridine (10 mg) in N,N-dimethylformamide (40 mL) was stirred at room temperature for 16 hours. The solvent was removed in vacuo and the residue was partitioned between ethyl acetate (100 mL) and water (100 mL). The organic phase was separated, washed with brine (50 mL), dried over sodium sulfate and concentrated in vacuo. Purification by column chromatography on silica gel, eluting with pentane:ethyl acetate, 75:25 to 67:33, afforded the title compound as a colourless oil in 75% yield, 6.50 g. 1HNMR (400 MHz, CDCl3) δ: 0.25 (6H, s), 0.97 (9H, s), 6.80 (1H, dd), 6.87 (1H, d), 7.84 (1H, d), 10.32 (1H, s)

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between ethyl acetate (100 mL) and water (100 mL)
  3. customThe organic phase was separated
  4. washwashed with brine (50 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customPurification by column chromatography on silica gel
  8. washeluting with pentane

Sources & evidence

ORD record
ord-ca0015b9261f445282b2d3b8cc057ac1
Source dataset
uspto-grants-2009_06
Patent number
US07547731B2

Reaction notes

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