Triethylsilane → Octanal, pentadecafluoro-

HRID 36462

Reaction equation

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]

Participants

Conditions

Temperature: 0 °C

Procedure

A sample of triethylsilane (4.24 g, 36.5 retool) 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 -25° 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).

Workup

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

Sources & evidence

ORD record: ord-781fb36c3c8e4434a89cb09b6ad5d670
Source dataset: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05414140

Linked notes

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