4-Hydroxybenzaldehyde → (4-((Tert-butyldimethylsilyl)oxy)phenyl)methanol

HRID 584389Notes

Reaction equation

HRID 584389 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[OH:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=[O:15])=[CH:12][CH:11]=1.N1C=CN=C1.CN(C)C=O>C(OCC)(=O)C.CCCCCC.O>[Si:1]([O:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][OH:15])=[CH:12][CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 10014460(4-((Tert-butyldimethylsilyl)oxy)phenyl)methanolYield 79.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Tert-butyldimethylsilyl chloride (24.1 g) was added to a mixture of 4-hydroxybenzaldehyde (17.8 g), imidazole (19.8 g) and N,N-dimethylformamide (100 ml). After stirring at room temperature for 2 hours, water was added and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The residue was dissolved in tetrahydrofuran (300 ml) and methanol (40 ml), and then sodium borohydride (11.1 g) was added in portions at 0° C. After stirring for 30 minutes, water was added and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The residue was subjected to silica gel chromatography to obtain 4-(tert-butyldimethylsilyloxy)benzylalcohol (27.7 g, yield 79%) as a colorless oil from an ethyl acetate-hexane (1:4, v/v)-eluted fraction.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in tetrahydrofuran (300 ml)
  6. additionmethanol (40 ml), and then sodium borohydride (11.1 g) was added in portions at 0° C
  7. stirringAfter stirring for 30 minutes
  8. additionwater was added
  9. extractionextracted with ethyl acetate
  10. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
  11. dry with materialdried (MgSO4)
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-3221b24a7dbb4c6ea6b509a03ec51106
Source dataset
uspto-grants-2005_08
Patent number
US06924300B2

Reaction notes

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