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

HRID 66402

反応式

HRID 66402 の反応式
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]

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

To a stirred solution of 0.020 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 (CDCl 3): 6.2 (d, ICH=) and 6.7 (quintuplet, =C-).

後処理

  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 (CDCl 3)

出典と根拠

ORDレコード
ord-ee8814a93a8044e3904426eff2a6053d
出典データセット
uspto-grants-1978_12
特許番号
US04131737

関連ノート

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