Tributylstannane → 3-(Tributylstannyl)-2-propenoic acid phenylmethyl ester

HRID 653951Notes

Reaction equation

HRID 653951 reaction equation
[C:1]1([CH2:7][O:8][C:9](=[O:12])[C:10]#[CH:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:13]([SnH:17]([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:18][CH2:19][CH2:20][CH3:21])[CH2:14][CH2:15][CH3:16]>N(C(C)(C)C#N)=NC(C)(C)C#N>[C:1]1([CH2:7][O:8][C:9](=[O:12])[CH:10]=[CH:11][Sn:17]([CH2:18][CH2:19][CH2:20][CH3:21])([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:13][CH2:14][CH2:15][CH3:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 5948TributylstannaneHCID 543064Benzyl propiolate

Product 1

HCID 679187483-(Tributylstannyl)-2-propenoic acid phenylmethyl esterYield 71.5%

Reagents, catalysts & solvents 1

HCID 6547AzobisisobutyronitrileCatalyst

Conditions

Temperature
65 °C

Procedure

To a stirring mixture of 2-propynoic acid phenylmethyl ester (2.46 g, 15.4 mmol) and tributyltin hydride (3.89 mL, 14.9 mmol, 97% purity) was added 2,2'-azobisisobutyronitrile (99.4 mg) and the reaction mixture was slowly warmed to 65° C. After stirring for 8 h at 65° C., the cooled reaction mixture was purified by flash chromatography, eluting with a mixture of hexane and EtOAc (50:1) to give 3-(tributylstannyl)-2-propenoic acid phenylmethyl ester (4.80 g, 10.65 mmol) as a mixture of E and Z isomers, in 69% yield.

Workup

  1. customthe cooled reaction mixture
  2. customwas purified by flash chromatography
  3. washeluting with a mixture of hexane and EtOAc (50:1)

Sources & evidence

ORD record
ord-4b8e6a01106a40d596697f163bf3268f
Source dataset
uspto-grants-1992_07
Patent number
US05128448

Reaction notes

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