Tributylstannane → HCID 12801789, compound

HRID 1995454Notes

Reaction equation

HRID 1995454 reaction equation
[CH2:1]([SnH:5]([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:6][CH2:7][CH2:8][CH3:9])[CH2:2][CH2:3][CH3:4].[F:14][C:15]([C:17]([O:25][Si:26]([CH3:29])([CH3:28])[CH3:27])([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:18][C:19]#[CH:20])=[CH2:16].N(C(C)(C)C#N)=NC(C)(C)C#N>>[F:14][C:15]([C:17]([O:25][Si:26]([CH3:29])([CH3:27])[CH3:28])([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:18]/[CH:19]=[CH:20]/[Sn:5]([CH2:6][CH2:7][CH2:8][CH3:9])([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:1][CH2:2][CH2:3][CH3:4])=[CH2:16]

Participants

4

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 12801788{[4-(1-Fluoroethenyl)oct-1-yn-4-yl]oxy}(trimethyl)silane

Product 1

HCID 12801789HCID 12801789, compound

Conditions

Temperature
140 °C

Procedure

A mixture of 21.4 ml. of tributylstannane, 18.3 g. of 4-(1'-fluorovinyl)-4-trimethylsilyloxy-1-octyne and azobisisobutyronitrile is heated under an inert atmosphere on an oil bath. Upon reaching 85° C. a rapid exotherm occurs which is moderated to maintain 140° C. using a water bath. After the exotherm the mixture is heated at 135° C. for one hour, then cooled to room temperature. The resulting oil is distilled via a Kugelrohr to give the desired product as 33.68 g. of a light yellow liquid (air bath 160° C., 0.15 mm.).

Workup

  1. additionA mixture of 21.4 ml
  2. customUpon reaching 85° C.
  3. temperatureAfter the exotherm the mixture is heated at 135° C. for one hour
  4. temperaturecooled to room temperature
  5. distillationThe resulting oil is distilled via a Kugelrohr

Sources & evidence

ORD record
ord-fa4b20dab1f94e47ade41b31739af915
Source dataset
uspto-grants-1983_09
Patent number
US04404393

Reaction notes

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