Iodine → 1-Iodo-4-trimethylsiloxy-trans-1-octene

HRID 2083529Notes

Reaction equation

HRID 2083529 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

7

Reactant 5

HCID 807IodineHCID 1145Trimethylamine oxideHCID 14798Sodium HydroxideHCID 192733Bis(1,2-dimethylpropyl)boraneHCID 12786181Trimethyl[(oct-1-yn-4-yl)oxy]silane

Product 1

HCID 128512771-Iodo-4-trimethylsiloxy-trans-1-octene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a stirred solution of 0.20 moles of freshely 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 (CDDl3): 6.2 (d, ICH=) and 6.7 (quintuplet, =CH--).

Workup

  1. temperaturecooled in an ice bath
  2. stirringThe mixture is stirred several hours at 25°-40° C
  3. customAfter 0.5 hour the organic phase is-separated
  4. extractionthe aqueous phase is extracted with ether
  5. washThe combined organic layers are washed with water, sodium thiosulfate solution, and brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationand concentrated
  8. customto give an oil, pmr spectrum (CDDl3)

Sources & evidence

ORD record
ord-4b3c9c34391c48799de98789fbb59c8f
Source dataset
uspto-grants-1978_04
Patent number
US04085272

Reaction notes

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