Allyltributylstannane → HCID 86685237, compound

HRID 1620998Notes

Reaction equation

HRID 1620998 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9](=[O:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[CH2:16]([Sn](CCCC)(CCCC)CCCC)[CH:17]=[CH2:18]>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([OH:15])([CH2:18][CH:17]=[CH2:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 2

HCID 90628AllyltributylstannaneHCID 2736412ethyl 3,4-dichlorophenylglyoxylate

Product 1

HCID 86685237HCID 86685237, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To the solution of ethyl 2-(3,4-dichlorophenyl)-2-oxoacetate (100 g, 3.8 mol) in CH2Cl2 was added allyltributyltin (1.2 equivalents) and TiCl4 (1.2 equivalents) at 0° C. and mixture was stirred for 40 hours at 0° C. to room temperature. Purification by chromatography on silica gel provided title compound (90 g, 77%).

Workup

  1. customPurification by chromatography on silica gel

Sources & evidence

ORD record
ord-0c2ae64b9eb9488ca313888349ff506c
Source dataset
uspto-grants-2014_07
Patent number
US08772500B2

Reaction notes

Loading…