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

HRID 362368Notes

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, giving 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-60868fd3382246ad89480e7f76a748a1
Source dataset: uspto-grants-1999_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05869483

Reaction notes

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