Imidazole → Tert-butyl-hex-5-enyloxy-dimethyl-silane
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
Product 1
Reagents, catalysts & solvents 1
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
- customthe two phases separated
- extractionThe aq. phase was extracted with ether
- dry with materiallayers were dried over MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-275f0dbd67ea4aeaab698bfe230a815f
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08114867B2
Reaction notes
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