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

HRID 848892

반응식

HRID 848892 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 80711,2-Dimethoxyethane용매2회

반응 조건

온도
25 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1de928bbe7f44bea988cead2cbf31c12
출처 데이터셋
uspto-grants-1981_10
특허 번호
US04297516

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