Iodine → 1-Iodo-4-trimethylsiloxy-trans-1-octene
Reaction equation
CC(C)C(BC(C(C)C)C)C.[CH3:12][Si:13]([CH3:24])([CH3:23])[O:14][CH:15]([CH2:19][CH2:20][CH2:21][CH3:22])[CH2:16][C:17]#[CH:18].C[N+]([O-])(C)C.[OH-].[Na+].[I:32]I>O1CCCC1>[I:32]/[CH:18]=[CH:17]/[CH2:16][CH:15]([O:14][Si:13]([CH3:23])([CH3:24])[CH3:12])[CH2:19][CH2:20][CH2:21][CH3:22]Participants
Procedure
To a stirred solution of 0.20 moles of freshly prepared bis-(3-methyl-2-butyl)borane in 300 ml of tetrahydrofuran at 0°-5° C. is added dropwise a solution of 19.8 g of 4-trimethylsiloxy-1-octyne in 30 ml of tetrahydrofuran. The resulting mixture is stirred at ambient temperature for several hours, cooled in an ice bath, and treated with 53 g of trimethylamine oxide. The mixture is stirred several hours at 25°-40° C. and then poured into 2 liters of 15% sodium hydroxide. The resulting mixture is treated immediately with a solution of 140 g of iodine in 300 ml of tetrahydrofuran. After 0.5 hour the organic phase is separated and the aqueous phase is extracted with ether. The combined organic layers are washed with water, sodium thiosulfate solution, and brine; dried over magnesium sulfate; and concentrated to give an oil, pmr spectrum (CDCl3): 6.2 (d, ICH=) and 6.7 (quintuplet, =H--).
Workup
- temperaturecooled in an ice bath
- stirringThe mixture is stirred several hours at 25°-40° C.
- customAfter 0.5 hour the organic phase is separated
- extractionthe aqueous phase is extracted with ether
- washThe combined organic layers are washed with water, sodium thiosulfate solution, and brine
- dry with materialdried over magnesium sulfate
- concentrationand concentrated
- customto give an oil, pmr spectrum (CDCl3)
Sources & evidence
- ORD record
- ord-432ceeb6401b4cc0becb13adb90e73c0
- Source dataset
- uspto-grants-1985_05
- Patent number
- US04518790
Reaction notes
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