Tributyltin Chloride → Stannane, tributyl-3-furanyl-

HRID 1003266

Reaction equation

Br[C:2]1[CH:6]=[CH:5][O:4][CH:3]=1.C([Li])CCC.[CH2:12]([Sn:16](Cl)([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:17][CH2:18][CH2:19][CH3:20])[CH2:13][CH2:14][CH3:15]>C(OCC)C.C(=O)([O-])O.[Na+]>[CH2:21]([Sn:16]([CH2:12][CH2:13][CH2:14][CH3:15])([CH2:17][CH2:18][CH2:19][CH3:20])[C:2]1[CH:6]=[CH:5][O:4][CH:3]=1)[CH2:22][CH2:23][CH3:24]

Participants

Conditions

Temperature: -76 °C

Procedure

3-Bromofuran (1.23 ml) was dissolved in diethyl ether (15 ml) and cooled to -76° C. Butyllithium (8.5 ml, 1.6M in hexane) was added dropwise ensuring the temperature remained below -60° C. After stirring for 15 minutes, tributyltin chloride (3.69 ml) was added. The reaction was stirred at -76° C. for 1 hour. The reaction was diluted with aqueous sodium hydrogencarbonate (20 ml) and the product extracted with diethyl ether (3×20 ml). The combined organic fractions were dried (brine, MgSO4) and concentrated in vacuo. The residue was purified by chromatography on silica eluting with hexane to yield the title compound as a colourless oil. 1H NMR (CDCl3, 360 MHz), δ 0.91 (9H, t, J 8.9 Hz), 1.03 (6H, t, J 10.4 Hz), 1.34 (6H, sx, J 7.3 Hz), 1.58 (6H, m), 6.35 (1H, d, J 1.5 Hz), 7.23 (1H, s), 7.56 (1H, t, J 1.4 Hz).

Workup

customremained below -60° C
stirringThe reaction was stirred at -76° C. for 1 hour
extractionthe product extracted with diethyl ether (3×20 ml)
dry with materialThe combined organic fractions were dried (brine, MgSO4)
concentrationconcentrated in vacuo
customThe residue was purified by chromatography on silica eluting with hexane

Sources & evidence

ORD record: ord-30003818a67d4e8c87ebcbef025b31c9
Source dataset: uspto-grants-2000_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06046195

Linked notes

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