Tin tetrachloride → (2-Butyl-3-benzo[b]furanyl) (5-methoxy-2-thienyl)methanone
Reaction equation
[CH2:1]([C:5]1[O:9][C:8]2[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=2[CH:6]=1)[CH2:2][CH2:3][CH3:4].[CH3:14][O:15][C:16]1[S:20][C:19]([C:21](Cl)=[O:22])=[CH:18][CH:17]=1.Cl[Sn](Cl)(Cl)Cl>C(Cl)(Cl)Cl>[CH2:1]([C:5]1[O:9][C:8]2[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=2[C:6]=1[C:21]([C:19]1[S:20][C:16]([O:15][CH3:14])=[CH:17][CH:18]=1)=[O:22])[CH2:2][CH2:3][CH3:4]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
3.0 g (17.2 mmol) 2-butylbenzo[b]furan were dissolved in 30 ml abs. chloroform, the solution was cooled to 0° C., and reacted with 3.6 g (20.4 mmol) 5-methoxy-2-thiophenecarbonyl chloride, dissolved in 5 ml abs. chloroform, and then, at a temperature between 0° and 3° C., 2.8 ml SnCl4 were added dropwise. Stirring for 2 hours at 0° C. followed. The reaction mixture was evacuated under ice-cooling over 50 ml 2N HCl, the phases were separated and the aqueous phase thoroughly extracted with ether. The chloroform and ether phases were each washed with 50 ml 2N NaOH, combined, dried over sodium sulphate and evaporated. The crude product was quickly distilled.
Workup
- dissolutiondissolved in 5 ml abs
- customThe reaction mixture was evacuated under ice-
- temperaturecooling over 50 ml 2N HCl
- customthe phases were separated
- extractionthe aqueous phase thoroughly extracted with ether
- washeach washed with 50 ml 2N NaOH
- dry with materialdried over sodium sulphate
- customevaporated
- distillationThe crude product was quickly distilled
Sources & evidence
- ORD record
- ord-3a67cd2fe798453f90f8e3841c0c8efd
- Source dataset
- uspto-grants-1992_03
- Patent number
- US05100911
Reaction notes
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