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

HRID 127075

반응식

HRID 127075 반응식
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]

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

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, =CH--).

후처리

  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 (CDCl3)

출처 및 근거

ORD 기록
ord-cd53418e1b744ba4a3003cd35c9a0eb4
출처 데이터셋
uspto-grants-1981_03
특허 번호
US04254285

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