Tributyltin Chloride → HCID 15288192, compound
Reaction equation
[CH3:1][C:2]1([CH3:12])[CH2:6][O:5][C:4]([C:7]2[S:8][CH:9]=[CH:10][CH:11]=2)=[N:3]1.C([Li])CCC.[CH2:18]([Sn:22](Cl)([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:23][CH2:24][CH2:25][CH3:26])[CH2:19][CH2:20][CH3:21]>CCOCC>[CH3:1][C:2]1([CH3:12])[CH2:6][O:5][C:4]([C:7]2[S:8][CH:9]=[CH:10][C:11]=2[Sn:22]([CH2:23][CH2:24][CH2:25][CH3:26])([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:18][CH2:19][CH2:20][CH3:21])=[N:3]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -70 °C
Procedure
To a solution of 5.0 g of 4,5-dihydro-4,4-dimethyl-2-(2-thienyl)-oxazole in 20 ml of ether is added dropwise 18.75 ml of butyl lithium while maintaining the temperature at -70° C. with stirring under nitrogen. The reaction mixture is stirred at -70° C. for 15 minutes and 30 minutes at 0° C. The reaction mixture is cooled to -70° C. and 10.0 g of tributyl tin chloride added. The reaction mixture is quenched with water and extracted with ether. The organic layer is washed with water (2×100 ml), dried and evaporated in vacuo to give 17.4 g of residue which is purified by chromatography on silica gel by elution with 7:1 hexane:ethyl acetate to give 12.4 g of a yellowish oil. MS(M+H=472) the next step is example 19.
Workup
- stirringThe reaction mixture is stirred at -70° C. for 15 minutes and 30 minutes at 0° C
- temperatureThe reaction mixture is cooled to -70° C.
- customThe reaction mixture is quenched with water
- extractionextracted with ether
- washThe organic layer is washed with water (2×100 ml)
- customdried
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-921a9e43bfb84fe8b6ca8ed928200808
- Source dataset
- uspto-grants-1998_07
- Patent number
- US05780471
Reaction notes
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