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 grams 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 grams 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 grams of iodine in 300 ml of tetrahydrofuran. After about 0.5 hour the organic phase is separated; then 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, =CH--).
Workup
- temperaturecooled in an ice bath
- stirringThe mixture is stirred several hours at 25°-40° C.
- customAfter about 0.5 hour the organic phase is separated
- extractionthen the 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-4680c3d001d241218968b52d7a2c9b63
- Source dataset
- uspto-grants-1981_02
- Patent number
- US04250325
Reaction notes
Loading…