Imidazole → Tert-butyl-hex-5-enyloxy-dimethyl-silane

HRID 1640511Notes

Reaction equation

HRID 1640511 reaction equation
[CH2:1]([OH:7])[CH2:2][CH2:3][CH2:4][CH:5]=[CH2:6].[CH3:8][C:9]([Si:12](Cl)([CH3:14])[CH3:13])([CH3:11])[CH3:10].N1C=CN=C1.O>C1COCC1>[C:9]([Si:12]([O:7][CH2:1][CH2:2][CH2:3][CH2:4][CH:5]=[CH2:6])([CH3:14])[CH3:13])([CH3:11])([CH3:10])[CH3:8]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 699635-Hexen-1-ol

Product 1

HCID 11085343Tert-butyl-hex-5-enyloxy-dimethyl-silaneYield 104.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-hexen-1-ol (5 g, 50 mmol) in THF (80 mL) were sequentially added TBDMSCl (8.4 g, 55 mmol) and imidazole (4.01 g, 60 mmol). The mixture was stirred at rt overnight. Water was added and the two phases separated. The aq. phase was extracted with ether and the combined org. layers were dried over MgSO4 and concentrated to give the title intermediate as a colourless liquid (11.2 g, 100% yield).

Workup

  1. customthe two phases separated
  2. extractionThe aq. phase was extracted with ether
  3. dry with materiallayers were dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-275f0dbd67ea4aeaab698bfe230a815f
Source dataset
uspto-grants-2012_02
Patent number
US08114867B2

Reaction notes

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