Tributylstannane → HCID 12786208, compound

HRID 848902Notes

Reaction equation

HRID 848902 reaction equation
[F:1][CH2:2][C:3]([O:11][Si:12]([CH3:15])([CH3:14])[CH3:13])([CH2:7][CH2:8][CH2:9][CH3:10])[CH2:4][C:5]#[CH:6].[CH2:16]([SnH:20]([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:21][CH2:22][CH2:23][CH3:24])[CH2:17][CH2:18][CH3:19].N(C(C)(C)C#N)=NC(C)(C)C#N>>[F:1][CH2:2][C:3]([O:11][Si:12]([CH3:15])([CH3:13])[CH3:14])([CH2:7][CH2:8][CH2:9][CH3:10])[CH2:4]/[CH:5]=[CH:6]/[Sn:20]([CH2:21][CH2:22][CH2:23][CH3:24])([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:16][CH2:17][CH2:18][CH3:19]

Participants

4

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 21764790HCID 21764790, compound

Product 1

HCID 12786208HCID 12786208, compound

Conditions

Temperature
120 °C

Procedure

A solution of 6.36 g. of 4-fluoromethyl-4-trimethylsilyloxy-1-octyne, 11.64 g. (10.6 ml.) of tributylstannane and 40 mg. of azobisisobutyronitrile is heated and stirred at 120° C. under nitrogen for 3 hours. The mixture is cooled, filtered through Celite and washed with hexanes. The hexanes are removed in vacuo and the residual liquid in vacuum distilled through a short path. The product is obtained at b.p. 110°-135° C./0.2-0.25 mm. (The product contains a minor amount of cis isomer.)

Workup

  1. temperatureThe mixture is cooled
  2. filtrationfiltered through Celite
  3. washwashed with hexanes
  4. customThe hexanes are removed in vacuo
  5. distillationthe residual liquid in vacuum distilled through a short path
  6. customThe product is obtained at b.p. 110°-135° C./0.2-0.25 mm

Sources & evidence

ORD record
ord-0d794f63bf8347e68edd6304ee1d8599
Source dataset
uspto-grants-1981_10
Patent number
US04297516

Reaction notes

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