Tributylstannane → HCID 6082810, compound

HRID 2251741Notes

Reaction equation

HRID 2251741 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].[C:14]1([C:20]#[CH:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>N(C(C)(C)C#N)=NC(C)(C)C#N>[CH2:10]([Sn:5]([CH2:1][CH2:2][CH2:3][CH3:4])([CH2:6][CH2:7][CH2:8][CH3:9])/[CH:21]=[CH:20]/[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:11][CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 5948TributylstannaneHCID 10821Phenylacetylene

Product 1

HCID 6082810HCID 6082810, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6547AzobisisobutyronitrileCatalyst

Conditions

Temperature
50 °C

Procedure

The synthesis was carried out according to the methods described in (a) Labadie, J. W.; Tueting, D.; Stille, J. K. J. Org. Chem. 1983, 48, 4634 and (b) Lappert, M. F.; Jones, K. J. Organomet. Chem. 1965, 3, 295. A mixture of tributyltin hydride (5.82 g, 20.0 mmole), phenylacetylene (1.95 g, 19.0 mmole), and 2,2′-azobis(isobutyronitrile) (0.14 g, 0.085 mmole) was slowly heated to 50° C., followed by stirring for 24 hours. Next, the mixture was cooled to room temperature and filtered by a Celite pad to remove the white precipitate. The filtrate was distilled to obtain 6.50 g of tributyl[(E)-2-phenyl-1-ethenyl]stannane. Yield: 84%.

Workup

  1. temperatureNext, the mixture was cooled to room temperature
  2. filtrationfiltered by a Celite pad
  3. customto remove the white precipitate
  4. distillationThe filtrate was distilled

Sources & evidence

ORD record
ord-61de73f346a446728f5f14f4d3a67b90
Source dataset
uspto-grants-2008_01
Patent number
US07320834B2

Reaction notes

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