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

HRID 1936923Notes

Reaction equation

HRID 1936923 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>[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

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 108791334-{[tert-Butyl(dimethyl)silyl]oxy}benzaldehydeYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 4-hydroxybenzaldehyde, Compound 63 (10.00 g, 81.89 mmol) and imidazole (16.72 g, 245.59 mmol) in dry DMF (30 mL) cooled in an ice-water bath (0° C.) was added a solution of t-butyldimethylsilyl chloride (18.55 g, 123.07 mmol) in dry DMF (50 mL) followed by stirring at room temperature for 1 hour. The reaction mixture was then quenched with brine (60 mL) and extracted with Et2O (60 mL×3). The combined organic layer was dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel, 5 percent EtOAc in hexane) to give Compound 64 (19.02 g, 98 percent): pale yellow oil; Rf=0.44 (10 percent EtOAc in hexane); IR (neat) 2956, 2931, 1698, 1598, 1273, 1156 cm−1; 1H NMR (300 MHz, CDCl3) δ9.89 (s, 1H), 7.81-7.77 (AA′BB′, 2H), 6.96-6.92 (AA′BB′, 2H), 0.98 (s, 9H), 0.25 (s, 6H); 13C NMR (75 MHz, CDCl3) δ190.9, 161.5, 131.9, 130.4, 120.5, 25.5, 18.2, −4.4; MS (+CI) m/z (relative intensity) 237 (M+H+, 100).

Workup

  1. customThe reaction mixture was then quenched with brine (60 mL)
  2. extractionextracted with Et2O (60 mL×3)
  3. dry with materialThe combined organic layer was dried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash column chromatography (silica gel, 5 percent EtOAc in hexane)

Sources & evidence

ORD record
ord-b58e8a7f82cb4cf8832e0a2a7a4e4272
Source dataset
uspto-grants-2002_05
Patent number
US06391916B1

Reaction notes

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