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

HRID 886648Notes

Reaction equation

HRID 886648 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].C(N(CC)CC)C>C1COCC1>[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

5

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 112071113-(t-Butyldimethylsilyloxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-hydroxybenzaldehyde (12.21 g, 100 mmol) in 600 mL THF was added tert-butyldimethylsilyl chloride (TBDMSCl, 18.84 g, 125 mmol). The solution was cooled to 0° C. and triethylamine (12.65 g, 17.4 mL, 125 mmol) was added dropwise. The reaction mixture was brought to room temperature and stirred 5 h. The mixture was filtered and the THF removed under reduced pressure. The oil was repeatedly dissolved in 200 mL portions of THF and evaporated, until no more triethylamine hydrochloride precipitated. The oil was then dissolved in 150 mL diethyl ether, filtered through a plug of neutral alumina and activated charcoal to remove the salt and the yellow color, and evaporated. The colorless, mobile oil was dried in vacuo overnight. Yield: 21.43 g (91%). IR: 1703, 1583, 1482, 1278, 1145, 840 cm-1. 1H NMR (CDCl3, TMS) δ 9.927 (s, 1H), 7.447 (d, J) 7.50 Hz, 1H), 7.379-7-335 (m, 2H), 7.096-7.074 (m, 1H), 0.994 (s, 9H), 0.215 (s, 6H). 13C NMR (CDCl3, TMS) δ 191.60, 156.34, 138.03, 130.03, 126.34, 123.46, 119.70, 25, 59, 18.12, −4.52. Anal. Calcd. for Cl3H20O2Si: C, 66.05; H, 8.53. Found: C, 66.13; H, 8.53.

Workup

  1. customwas brought to room temperature
  2. filtrationThe mixture was filtered
  3. customthe THF removed under reduced pressure
  4. dissolutionThe oil was repeatedly dissolved in 200 mL portions of THF
  5. customevaporated, until no more triethylamine hydrochloride
  6. customprecipitated
  7. dissolutionThe oil was then dissolved in 150 mL diethyl ether
  8. filtrationfiltered through a plug of neutral alumina and activated charcoal
  9. customto remove the salt
  10. customthe yellow color, and evaporated
  11. customThe colorless, mobile oil was dried in vacuo overnight

Sources & evidence

ORD record
ord-fbe607da874141019a1b28394ce7b38d
Source dataset
uspto-grants-2012_08
Patent number
US08246869B2

Reaction notes

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