Tributylstannane → HCID 12786208, compound

HRID 903666Notes

Reaction equation

HRID 903666 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. of (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 is 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. distillationdistilled 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-56598e4b237f4191a83ff08e7c6fac78
Source dataset
uspto-grants-1980_10
Patent number
US04228298

Reaction notes

Loading…