Tributyltin Chloride → 2-(Tributylstannyl)-3-thienyl-1,3-dioxolane
Reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH:6]2[O:10][CH2:9][CH2:8][O:7]2)=[CH:2]1.C([Li])CCC.[CH2:16]([Sn:20](Cl)([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:21][CH2:22][CH2:23][CH3:24])[CH2:17][CH2:18][CH3:19]>CCOCC.O1CCCC1>[CH2:25]([Sn:20]([CH2:16][CH2:17][CH2:18][CH3:19])([CH2:21][CH2:22][CH2:23][CH3:24])[C:2]1[S:1][CH:5]=[CH:4][C:3]=1[CH:6]1[O:10][CH2:9][CH2:8][O:7]1)[CH2:26][CH2:27][CH3:28]Participants
6
Conditions
- Temperature
- -78 °C
Procedure
To a stirred solution of 15.6 g of 2-(3-thienyl)-1,3-dioxolane in 100 ml of anhydrous ether is added dropwise 74.3 ml of 1.48 N n-butyllithium under nitrogen at room temperature. After 15 minutes at reflux, the reaction mixture is cooled to -78° C. and 34.18 g of tri-n-butyltin chloride in 100 ml of dry tetrahydrofuran is added dropwise. After the addition is complete, the mixture is warmed to room temperature and the solvent is evaporated in vacuo to an oily residue. To the residue is added 100 ml of hexane and the resulting precipitate of lithium chloride collected. The filtrate is concentrated in vacuo to a residue which is distilled at 160°/0.04 mm Hg to give 34.16 g of the desired product.
Workup
- temperatureAfter 15 minutes at reflux
- additionAfter the addition
- temperaturethe mixture is warmed to room temperature
- customthe solvent is evaporated in vacuo to an oily residue
- additionTo the residue is added 100 ml of hexane
- customthe resulting precipitate of lithium chloride collected
- concentrationThe filtrate is concentrated in vacuo to a residue which
- distillationis distilled at 160°/0.04 mm Hg
Sources & evidence
- ORD record
- ord-0258e55da0f34fc1aef8b10787da227a
- Source dataset
- uspto-grants-1995_07
- Patent number
- US05436333
Reaction notes
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