Imidazole → 4-(Dimethyl-tert-butylsilyl)oxybutan-1-ol

HRID 327349

Reaction equation

HRID 327349 reaction equation
[CH2:1]([OH:6])[CH2:2][CH2:3][CH2:4][OH:5].[Si:7](Cl)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8].N1C=CN=C1.C(OCC)(=O)C>C1COCC1.O>[Si:7]([O:5][CH2:4][CH2:3][CH2:2][CH2:1][OH:6])([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 80641,4-ButanediolHCID 8857Ethyl AcetateHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 1864034-(Dimethyl-tert-butylsilyl)oxybutan-1-olYield 66.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1,4-butanediol (10.54 g, 0.117 mol) in dry THF (100 mL) was treated with t-butyl dimethylsilylchloride (17.30 g, 0.114 mol) and imidazole (7.80 g, 0.114 mol). After 2 h at room temperature, work-up with ethyl acetate and water, followed by drying the organic phase and concentration, gave a crude product that was purified by silica gel flash chromatography (being eluted with 20% ethyl acetate in hexane) to yield 15.5 g (Y: 65%) of 4-(t-butyldimethylsilyloxy)-1-butanol (XXVIIa) as a colorless oil; 1H-NMR (CDCl3, 300 MHz) δ ppm: 3.58 (m, 4H) 1.58 (m, 4H) 0.84 (s, 9H) 0.01 (s, 6H).

Workup

  1. customby drying
  2. concentrationthe organic phase and concentration
  3. customgave a crude product that
  4. customwas purified by silica gel flash chromatography (being eluted with 20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-d6628943fa9846129d186856ab16d51b
Source dataset
uspto-grants-1993_12
Patent number
US05272171

Linked notes

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