1-Butanol, 4-[[(1,1-dimethylethyl)diphenylsilyl]oxy]- → 4-(Tert-butyldiphenylsilyloxy)butanal

HRID 1643305Notes

Reaction equation

HRID 1643305 reaction equation
C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O.[C:12]([Si:16]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[O:17][CH2:18][CH2:19][CH2:20][CH2:21][OH:22])([CH3:15])([CH3:14])[CH3:13]>C(Cl)Cl>[C:12]([Si:16]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[O:17][CH2:18][CH2:19][CH2:20][CH:21]=[O:22])([CH3:15])([CH3:13])[CH3:14]

Participants

4

Reactant 2

HCID 100651081-Butanol, 4-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-HCID 178418287HCID 178418287, compound

Product 1

HCID 108711124-(Tert-butyldiphenylsilyloxy)butanalYield 78.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 9.0 g silica gel and PCC (7.7 g, 35.7 mmol) in 300 mL DCM was added 4-(tert-Butyl-diphenyl-silanyloxy)-butan-1-ol (6.0 g, 18.3 mmol) in 50 mL DCM. The mixture was stirred for 3 h at room temperature and then the resulting suspension filtered thorough a pad of celite/florisil and rinsed with DCM. The solvent was evaporated and the product was isolated by flash column chromatography eluting with 0% to 30% ethyl acetate/hexane to give the title compound (4.7 g) as a light yellow oil.

Workup

  1. filtrationthe resulting suspension filtered thorough a pad of celite/florisil
  2. washrinsed with DCM
  3. customThe solvent was evaporated
  4. customthe product was isolated by flash column chromatography
  5. washeluting with 0% to 30% ethyl acetate/hexane

Sources & evidence

ORD record
ord-d732016c83f245f286fb994b283d8bfa
Source dataset
uspto-grants-2012_02
Patent number
US08119692B2

Reaction notes

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