Imidazole → 1-[(Tert-butyldimethylsilyl)oxy]but-3-en-2-ol

HRID 2103746

Reaction equation

HRID 2103746 reaction equation
[CH2:1]([OH:6])[CH:2]([OH:5])[CH:3]=[CH2:4].N1C=CN=C1.[Si:12](Cl)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]>C(Cl)Cl.[NH4+].[Cl-]>[C:15]([Si:12]([CH3:14])([CH3:13])[O:6][CH2:1][CH:2]([OH:5])[CH:3]=[CH2:4])([CH3:18])([CH3:17])[CH3:16]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 103383-Butene-1,2-diolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 109105951-[(Tert-butyldimethylsilyl)oxy]but-3-en-2-olYield 72.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (+/−)-3-butene-1,2-diol (500 mg, 5.67 mmol) in CH2Cl2 (25 mL) was added imidazole (444 mg, 6.53 mmol). The solution was cooled to 0° C. and t-butyidimethylsilyl chloride (1.0 M in THF, 6.24 mL, 6.24 mmol) was added. The reaction was stirred at 0° C. for 15 minutes and at room temperature for 1 hour and 30 minutes. The mixture was diluted with aqueous NH4Cl and extracted with CH2Cl2 (3×). The organic solution was washed with brine, dried (MgSO4), filtered and concentrated. The residue was purified by medium pressure chromatography eluting with a solvent gradient (5% EtOAc in hexanes to 100% EtOAc) to provide 827.5 mg of 1-(tert-butyl-dimethyl-silanyloxy)-but-3-en-2-ol. 1H NMR (CDCl3) δ 5.81 (m, 1H), 5.34 (d, 1H), 5.19 (d, 1H), 4.17 (m, 1H), 3.66 (dd, 1H), 3.45 (dd, 1H), 0.90 (s, 9H), 0.08 (s, 6H); MS m/z 202.

Workup

  1. extractionextracted with CH2Cl2 (3×)
  2. washThe organic solution was washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by medium pressure chromatography
  7. washeluting with a solvent gradient (5% EtOAc in hexanes to 100% EtOAc)

Sources & evidence

ORD record
ord-f3ec14cbb1ab46e98c134b9789cb9970
Source dataset
uspto-grants-2009_08
Patent number
US07576128B2

Linked notes

Loading…