Triethylsilane → Octanal, pentadecafluoro-

HRID 864613

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HRID 864613 반응식
C([SiH](CC)CC)C.[F:8][C:9]([F:32])([C:13]([F:31])([F:30])[C:14]([F:29])([F:28])[C:15]([F:27])([F:26])[C:16]([F:25])([F:24])[C:17]([F:23])([F:22])[C:18]([F:21])([F:20])[F:19])[C:10](Cl)=[O:11]>[Pd].C([SiH](CC)CC)C>[C:9]([CH:10]=[O:11])([C:13]([C:14]([C:15]([C:16]([C:17]([C:18]([F:19])([F:20])[F:21])([F:22])[F:23])([F:25])[F:24])([F:27])[F:26])([F:29])[F:28])([F:31])[F:30])([F:32])[F:8]

참가 물질

5

반응물 2

HCID 12052Triethylsilane2회HCID 78978Perfluorooctanoyl chloride

생성물 1

HCID 533723Octanal, pentadecafluoro-수율 112.9%

시약·촉매·용매 2

HCID 12052Triethylsilane촉매HCID 23938Palladium촉매

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온도
0 °C

실험 절차

A sample of triethylsilane (4.24 g, 36.5 mmol) was cooled to 0° C. and treated with 10% Pd/C (0.35 g). After the exotherm subsided, perfluorooctanoyl chloride (15.8 g, 36.5 mmol) was added dropwise, controlling the temperature below ca. 6°-8° C. The mixture was stirred for 1.0 hr at 0° C. Another 0.59 g triethylsilane was added, and the mixture was stirred for 1.5 hr. An additional 0.13 g of triethylsilane was added. After 1.0 hr, vacuum transfer gave 16.4 g of liquid which was cooled at -250°C. for several hours. The top liquid layer was removed from the solid to provide ca. 10.5 g of the titled product. 19F NMR: -81.3 (t of t's, J=9.8, 2.3), -121.8 (m), -122.3 (m), -123.0 (m), 123.7 (m), -125.4 (t of m's, with JFCCH =3 Hz ), -126.5 (m).

후처리

  1. customthe temperature below ca. 6°-8° C
  2. stirringthe mixture was stirred for 1.5 hr
  3. waitAfter 1.0 hr

출처 및 근거

ORD 기록
ord-08de88032f0846ce95f6a93dd44b7791
출처 데이터셋
uspto-grants-1996_10
특허 번호
US05563235

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