Tributylstannane → HCID 14675643, compound

HRID 2352302Notes

Reaction equation

HRID 2352302 reaction equation
Cl[CH:2]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:3][C:4]([F:8])=[C:5]([F:7])[F:6].C([SnH](CCCC)CCCC)CCC>>[F:6][C:5]([F:7])=[C:4]([F:8])[CH2:3][CH2:2][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

3

Reactant 2

HCID 5948TributylstannaneHCID 14675642HCID 14675642, compound

Product 1

HCID 14675643HCID 14675643, compound

Procedure

A stirred mixture of 4.6 grams (0.0179 mole) of 4-chloro-1,1,2-trifluoro-1-dodecene (prepared as in Example 7) and 0.04 gram (0.0003 mole) of alpha, alpha-azobisisobutyronitrile is flushed with argon and 5.1 ml (0.019 mole) of tri-n-butyltin hydride is added dropwise. Upon completion of addition, the reaction mixture is stirred at ambient temperature for 16 hours. The reaction mixture is fractionally distilled under reduced pressure through a Vigreux column. The appropriate fractions are recombined and redistilled, again under reduced pressure and through a Vigreux column. The yield of 1,1,2-trifluoro-1-dodecene is 1.2 grams; b.p. 42°-45° C./0.45 mm. The nmr spectrum is consistent with the proposed structure. Analysis: calc'd for C12H21F3 : C 64.85, H 9.52; Found: C 64.82, H 9.32.

Workup

  1. additionis added dropwise
  2. additionUpon completion of addition
  3. distillationThe reaction mixture is fractionally distilled under reduced pressure through a Vigreux column
  4. distillationredistilled, again under reduced pressure and through a Vigreux column

Sources & evidence

ORD record
ord-bba2a206f2be48bea49af8f613025d2c
Source dataset
uspto-grants-1989_10
Patent number
US04876285

Reaction notes

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