Imidazole → 4-{[Tert-butyl(dimethyl)silyl]oxy}-2,2-dimethylbutan-1-ol

HRID 327350Notes

Reaction equation

HRID 327350 reaction equation
[CH3:1][C:2]([CH3:8])([CH2:5][CH2:6][OH:7])[CH2:3][OH:4].[Si:9](Cl)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10].N1C=CN=C1.C(OCC)(=O)C>C1COCC1.O>[Si:9]([O:7][CH2:6][CH2:5][C:2]([CH3:8])([CH3:1])[CH2:3][OH:4])([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 8857Ethyl AcetateHCID 28928tert-Butyldimethylsilyl chlorideHCID 108878792,2-Dimethylbutane-1,4-diol

Product 1

HCID 197346474-{[Tert-butyl(dimethyl)silyl]oxy}-2,2-dimethylbutan-1-olYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2,2-dimethyl-1,4-butanediol (8.01 g, 67.8 mmol) in dry THF (80 mL) was treated with t-butyldimethylsilyl chloride (10.2 g, 67.8 mmol) and imidazole (4.60 g, 67.6 mmol). After 24 h at room temperature, work-up with ethyl acetate and water followed by drying the organics and concentration gave a crude product, which was purified by silica gel flash chromatography (being eluted with 5% ethyl acetate in hexane) to afford 11.0 g (Y: 70%) of 4-t-butyldimethylsilyloxy-2,2-dimethyl-1-butanol (XXVIIb) as a colorless oil; 1H-NMR (DMSO-d6) δ ppm: 4.43 (t, 1H) 3.61 (t, 2H) 3.05 (d, J=2.7 Hz, 2H) 1.38 (t, 2H) 0.83 (s, 9H) 0.78 (s, 6H) 0.00(s, 6H); HRMS Calcd for C12H29O2Si (MH+): 233.1937, found: 233.1930.

Workup

  1. customby drying the organics and
  2. concentrationconcentration
  3. customgave a crude product, which
  4. customwas purified by silica gel flash chromatography (being eluted with 5% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-d3fb01486504488f909cf604fa102686
Source dataset
uspto-grants-1993_12
Patent number
US05272171

Reaction notes

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