Imidazole → 1-Iodo-3-methyl-3-trimethylsilyloxy-1-octene
Reaction equation
[OH:1][C:2]([CH3:11])([CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH:3]=[CH:4][I:5].N1C=CN=C1.[CH3:17][Si:18](Cl)([CH3:20])[CH3:19].CCCCCC>CN(C)C=O>[I:5][CH:4]=[CH:3][C:2]([CH3:11])([O:1][Si:18]([CH3:20])([CH3:19])[CH3:17])[CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a stirred solution of 11.7 g of 3-hydroxy-1-iodo-3-methyl-1octene (Example 184) and 7.4 of imidazole in 45 ml of dry dimethylformamide is added dropwise 5.98 g of trimethylsilylchloride at 0° C under argon atmosphere. After stirring at 0° C for an additional 15 minutes, the solution is stirred at ambient temperature for 18 hours. The reaction mixture is poured into 600 ml of hexane and the resulting solution washed with water, saturated sodium chloride solution, dried over anhydrous magnesium sulfate and taken to dryness to furnish 14.7 g of oil. Distillation affords 13.4 g of clear oil; bp 65° C (0.05 mm); λ max 6.21, 8.00, 9.90, 10.51, 11.90, 13.2μ.
Workup
- stirringthe solution is stirred at ambient temperature for 18 hours
- washthe resulting solution washed with water, saturated sodium chloride solution
- dry with materialdried over anhydrous magnesium sulfate
Sources & evidence
- ORD record
- ord-ef00f6cd739e4b08a02057c6a5c852b7
- Source dataset
- uspto-grants-1978_04
- Patent number
- US04085272
Reaction notes
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