Tributyltin Chloride → 2-(Tributylstannyl)-3-thienyl-1,3-dioxolane

HRID 1457631Notes

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.[CH2:11]([Sn:15](Cl)([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16][CH2:17][CH2:18][CH3:19])[CH2:12][CH2:13][CH3:14]>CCOCC.C([Li])CCC.O1CCCC1>[CH2:20]([Sn:15]([CH2:11][CH2:12][CH2:13][CH3:14])([CH2:16][CH2:17][CH2:18][CH3:19])[C:2]1[S:1][CH:5]=[CH:4][C:3]=1[CH:6]1[O:10][CH2:9][CH2:8][O:7]1)[CH2:21][CH2:22][CH3:23]

Participants

Conditions

Temperature: -78 °C

Procedure

To a stirred solution of 15.6 g (0.10 mol) of 2-(3-thienyl)-1,3-dioxolane in 100 ml of anhydrous ether, n-butyl-lithium (1.48N, in hexane, 74.3 ml) is added dropwise under nitrogen at room temperature. After being refluxed for 15 minutes, the reaction mixture is cooled to -78° C. and tri-n-butyltin chloride (34.18 g, 0.105 mol) in 100 ml of dry tetrahydrofuran is added dropwise. After the addition is complete, the mixture is warmed to room temperature and the solvent evaporated. To the oily residue 100 ml of hexane is added, and the resulting precipitate (LiCl) is filtered off. The filtrate is evaporated and the residue distilled at reduced pressure, given 34.16 g (77%) of the desired product.

Workup

temperatureAfter being refluxed for 15 minutes
additionAfter the addition
temperaturethe mixture is warmed to room temperature
customthe solvent evaporated
additionTo the oily residue 100 ml of hexane is added
filtrationthe resulting precipitate (LiCl) is filtered off
customThe filtrate is evaporated
distillationthe residue distilled at reduced pressure

Sources & evidence

ORD record: ord-69f9e7d585884e9997e76ec2c2d9e3b5
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05849735

Reaction notes

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