Imidazole → (E)-4-(tert-butyldimethylsilyloxy)but-2-en-1-ol

HRID 707673

Reaction equation

HRID 707673 reaction equation
[CH2:1]([OH:6])/[CH:2]=[CH:3]/[CH2:4][OH:5].N1C=CN=C1.[Si:12](Cl)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13].O>CN(C=O)C>[Si:12]([O:5][CH2:4]/[CH:3]=[CH:2]/[CH2:1][OH:6])([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 175854trans-2-Butene-1,4-diol

Product 1

HCID 13841129(E)-4-(tert-butyldimethylsilyloxy)but-2-en-1-olYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (2E)-2-butene-1,4-diol (8.22 mL, 0.10 mol) and imidazole (8.50 g, 0.125 mol) in DMF (50 mL) at 0° C., was added tert-butyldimethylsilyl chloride (7.50 g, 0.050 mol) in several portions over 10 minutes. The resulting mixture was warmed to room temperature and stirred (2 h), then poured into H2O (200 mL) and extracted with EtOAc (2×150 mL). The organic layer was washed (brine), dried (Na2SO4) and purified by silica gel column chromatography (hexanes:EtOAc) to yield 5 as a colorless oil (9.0 g, 89% yield). 1H NMR (400 MHz, CDCl3) δ 5.60-5.50 (m, 2H), 4.18 (m, 2H), 4.09 (m, 2H), 2.76 (br, 1H), 0.83 (s, 9H), 0.01 (s, 6H). 13C NMR (100 MHz, CDCl3) δ 136.3, 135.4, 64.8, 63.8, 31.1, 23.6.

Workup

  1. extractionextracted with EtOAc (2×150 mL)
  2. washThe organic layer was washed (brine)
  3. dry with materialdried (Na2SO4)
  4. custompurified by silica gel column chromatography (hexanes:EtOAc)

Sources & evidence

ORD record
ord-4e446db5c6ca4c47a2c5d3010fa598b3
Source dataset
uspto-grants-2015_11
Patent number
US09175038B2

Linked notes

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