Imidazole → 4-(tert-Butyl-diphenyl-silanyloxy)-but-2-en-1-ol

HRID 748789Notes

Reaction equation

HRID 748789 reaction equation
[CH2:1]([OH:6])[CH:2]=[CH:3][CH2:4][OH:5].N1C=CN=C1.[C:12]([Si:16](Cl)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([CH3:15])([CH3:14])[CH3:13].C(OCC)(=O)C>ClCCl.CN(C)C=O>[Si:16]([O:5][CH2:4][CH:3]=[CH:2][CH2:1][OH:6])([C:12]([CH3:15])([CH3:14])[CH3:13])([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 80652-Butene-1,4-diolHCID 8857Ethyl AcetateHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 666569494-(tert-Butyl-diphenyl-silanyloxy)-but-2-en-1-olYield 42%

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

In a dichloromethane/N,N-dimethylformamide (200 ml/200 ml) mixture were dissolved 2-buten-1,4-diol (10.0 g, 113 mmol) and imidazole (4.70 g, 69.0 mmol), followed by the dropwise addition of t-butylchlorodiphenylsilane (30.0 ml, 115 mmol) at room temperature. After completion of the dropwise addition, the mixture was stirred at room temperature for 4 days. The residue obtained by concentrating the reaction mixture under reduced pressure was added with diethyl ether. From the resulting mixture, the insoluble matter was filtered off. The diethyl ether layer was washed with water and then, the organic layer was dried over anhydrous magnesium sulfate. After fitration, the filtrate was concentrated under reduced pressure. The residue was subjected to flash silica gel chromatography, and the fraction obtained from the hexane:ethyl acetate=2:1 eluate was concentrated under reduced pressure, whereby the title compound (15.3 g, 46.9 mmol, 42%) was obtained as a colorless oil.

Workup

  1. additionAfter completion of the dropwise addition
  2. customThe residue obtained
  3. concentrationby concentrating the reaction mixture under reduced pressure
  4. additionwas added with diethyl ether
  5. filtrationFrom the resulting mixture, the insoluble matter was filtered off
  6. washThe diethyl ether layer was washed with water
  7. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  8. concentrationAfter fitration, the filtrate was concentrated under reduced pressure
  9. customthe fraction obtained from the hexane

Sources & evidence

ORD record
ord-cdac057bba9a459796121b333d8a2070
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

Loading…