Iodine → 1-Iodo-4-propadienyl-4-trimethylsilyloxy-trans-octene

HRID 126700

反応式

HRID 126700 の反応式
[CH:1]([C:4]([O:12][Si:13]([CH3:16])([CH3:15])[CH3:14])([CH2:8][CH2:9][CH2:10][CH3:11])[CH2:5][C:6]#[CH:7])=[C:2]=[CH2:3].CC(C)C(BC(C(C)C)C)C.C([N+]([O-])(CC)CC)C.[I:36]I>O1CCCC1.C(COC)OC>[I:36]/[CH:3]=[CH:2]/[CH2:1][C:4]([CH:5]=[C:6]=[CH2:7])([O:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[CH2:8][CH2:9][CH2:10][CH3:11]

参加物

7

反応物 4

HCID 807IodineHCID 123168Ethanamine, N,N-diethyl-, N-oxideHCID 192733Bis(1,2-dimethylpropyl)boraneHCID 130391894-Propadienyl-4-trimethylsilyloxy-1-octyne

生成物 1

HCID 130391901-Iodo-4-propadienyl-4-trimethylsilyloxy-trans-octene

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 80711,2-Dimethoxyethane溶媒2 回

反応条件

温度
25 °C

実験手順

To a stirred solution of 2.36 g. (10 mmol.) of 4-propadienyl-4-trimethylsilyloxy-1-octyne in 5 ml. of glyme is added a solution of 11 mmol. of bis-(3-methyl-2-butyl)borane in 15 ml. of glyme at 0° C. The mixture is stirred at 25° C. for 90 minutes, cooled to 0° C., and treated portionwise with 3.0 g. of triethylamine oxide. The stirred mixture is maintained at 25°-30° C. for 45 minutes, diluted with 20 ml. of tetrahydrofuran and poured into 100 ml. of ice-cold 15% sodium hydroxide solution, followed immediately with a solution of 8.0 g. of iodine in 20 ml. of tetrahydrofuran. The mixture is stirred at ambient temperature for 30 minutes and then extracted with ether. The extract is washed successively with water, sodium thiosulfate solution and brine; dried over magnesium sulfate; and filtered. The residue obtained after solvent evaporation is subjected to chromatography on silica gel with heptane solvent to afford the title compound as a liquid.

後処理

  1. customat 0° C
  2. temperaturecooled to 0° C.
  3. additiontreated portionwise with 3.0 g
  4. temperatureThe stirred mixture is maintained at 25°-30° C. for 45 minutes
  5. additiondiluted with 20 ml
  6. stirringThe mixture is stirred at ambient temperature for 30 minutes
  7. extractionextracted with ether
  8. washThe extract is washed successively with water, sodium thiosulfate solution and brine
  9. dry with materialdried over magnesium sulfate
  10. filtrationand filtered
  11. customThe residue obtained
  12. customafter solvent evaporation

出典と根拠

ORDレコード
ord-ef854b8b1a4b4db58fa8861e2b5a0364
出典データセット
uspto-grants-1981_03
特許番号
US04254036

関連ノート

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