Tributylstannane → HCID 12786228, compound

HRID 1277750Notes

Reaction equation

HRID 1277750 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([O:11][Si:12]([CH3:15])([CH3:14])[CH3:13])([CH:9]=[CH2:10])[CH2:6][C:7]#[CH:8].[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]>>[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([O:11][Si:12]([CH3:14])([CH3:13])[CH3:15])([CH:9]=[CH2:10])[CH2:6]/[CH:7]=[CH:8]/[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

3

Reactant 2

HCID 5948TributylstannaneHCID 12786227HCID 12786227, compound

Product 1

HCID 12786228HCID 12786228, compoundYield 80%

Conditions

Temperature
140 °C

Procedure

A mixture of 7-chloro-4-trimethylsilyloxy-4-vinyl-1-heptyne (17 g, 0.07 mol) and 20.7 g (0.71 mol) of tri-n-butylstannane and 150 mg of azobisisobutrylnitrile (AIBN) is stirred under argon in a 140° oil bath behind a safety shield. After 3 minutes an exotherm occurs and the mixture is maintained at 140° C. for 1.5 hr. After cooling, air is admitted and the unreacted tri-n-butylstannane is removed by distillation via Kuglerohr (140°, 0.5-0.3 mm) to give a very light yellow oil (30 g). This oil consists of a mixture of the E and Z isomers.

Workup

  1. temperatureAfter cooling
  2. customthe unreacted tri-n-butylstannane is removed by distillation via Kuglerohr (140°, 0.5-0.3 mm)

Sources & evidence

ORD record
ord-137c8803d9664f229705d1f801381941
Source dataset
uspto-grants-1981_07
Patent number
US04278806

Reaction notes

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