Imidazole → Tert-butyldimethylsilyloxybutan-2-ol

HRID 1751822Notes

Reaction equation

HRID 1751822 reaction equation
[CH2:1]([OH:6])[CH:2]([OH:5])[CH2:3][CH3:4].CN(C)C=O.[Si:12](Cl)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13].N1C=CN=C1>ClCCl>[Si:12]([O:6][CH2:1][CH:2]([OH:5])[CH2:3][CH3:4])([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 114291,2-ButanediolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 21640814Tert-butyldimethylsilyloxybutan-2-olYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 50 mL round bottom flask was charged with (±)-1,2-butanediol (1 g, 11.09 mmol) and to it was added dimethylformamide (8 mL) followed by tert-butyldimethylsilyl chloride (2.5 g, 16.64 mmol) and imidazole (1.88 g, 27.7 mmol). The reaction mixture was stirred for 10 hours after which it was diluted with dichloromethane and poured into a separatory funnel and washed with water (80 mL) and brine and dried over magnesium sulfate. After filtration and concentration the crude oil was purified by silica gel flash chromatography (hexanes:ethylacetate) to obtain 1 gm of pure desired product in 45% yield. 1H(CDCl3) δ (ppm): 3.6 (m, 1H). 3.5 (m, 1H), 3.4 (m, 1H), 2.4 (s, 1H), 1.44 (m, 2H), 0.99 (t, 3H), 0.9 (s, 9H), 0.06 (s, 6H).

Workup

  1. additionpoured into a separatory funnel
  2. washwashed with water (80 mL) and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationAfter filtration and concentration the crude oil
  5. customwas purified by silica gel flash chromatography (hexanes:ethylacetate)

Sources & evidence

ORD record
ord-ff4c539008db461f9b490aff99763171
Source dataset
uspto-grants-2015_10
Patent number
US09161997B2

Reaction notes

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