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

HRID 741620Notes

Reaction equation

HRID 741620 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[Si:10](Cl)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11].N1C=CN=C1.O>CN(C)C=O>[Si:10]([O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6])([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]

Participants

6

Reactant 4

HCID 1013-HydroxybenzaldehydeHCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 112071113-(t-Butyldimethylsilyloxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Hydroxybenzaldehyde (70 g, 0.57 mol), tert-butyldimethylsilyl chloride (92 g, 0.61 mol), and imidazole (92 g, 1.35 mol) were combined in dimethylformamide (250 mL). The mixture was stirred at room temperature, under nitrogen, for 1 hour. The solution was poured into water (1.5 L) and extracted with 2×500 mL petroleum ether (35°-60° C. boiling range). The organic solution was washed with saturated sodium chloride solution (100 mL), dried over magnesium sulfate, treated with silica gel (20 g), filtered, and concentrated in vacuo. The residue was dried further under high vacuum to yield 126.6 g (94%) of the air and light-sensitive 3-((tert-butyldimethylsilyl)oxy)benzaldehyde as an amber oil. NMR (300 MHz, CDCl3): δ0.22 (s, 6H); 0.99 (s, 9H); 7.10 (ddd, J1 =1.2 Hz, J2 =2.5 Hz, J3 =7.9 Hz, 1H); 7.32 (dd, J1 =1.5 Hz, J2 =2.4 Hz, 1H); 7.39 (t, J=7.8 Hz, 1H); 7.47 (ddd, J1 =1.3 Hz, J2 =1.3 Hz, J3 =7.6 Hz, 1H); 9.95 (s, 1H). Mass spectrum (CI--CH4) m/e: 237 (M+1, 100%). Calculated for C13H20O2Si: C, 66.05; H, 8.53. Found: C, 65.95; H, 8.56.

Workup

  1. extractionextracted with 2×500 mL petroleum ether (35°-60° C. boiling range)
  2. washThe organic solution was washed with saturated sodium chloride solution (100 mL)
  3. dry with materialdried over magnesium sulfate
  4. additiontreated with silica gel (20 g)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was dried further under high vacuum

Sources & evidence

ORD record
ord-59b025d46b24402eacfea2ca87cb9315
Source dataset
uspto-grants-1996_09
Patent number
US05552404

Reaction notes

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