Tributyltin Chloride → HCID 67060786, compound

HRID 410009Notes

Reaction equation

HRID 410009 reaction equation
[Li]CCCC.[O:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[C:11]1[O:12][CH:13]=[CH:14][CH:15]=1.[Sn:16](Cl)([CH2:25][CH2:26][CH2:27][CH3:28])([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:17][CH2:18][CH2:19][CH3:20]>C1COCC1>[CH2:25]([Sn:16]([CH2:17][CH2:18][CH2:19][CH3:20])([CH2:21][CH2:22][CH2:23][CH3:24])[C:7]1([C:11]2[O:12][CH:13]=[CH:14][CH:15]=2)[CH2:8][CH:9]=[CH:10][O:6]1)[CH2:26][CH2:27][CH3:28]

Participants

5

Reactant 3

HCID 15096Tributyltin ChlorideHCID 800062,2'-BifuranHCID 178418339Butyllithium

Product 1

HCID 67060786HCID 67060786, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of n-BuLi (7.7 mL, of 2.5M in hexanes, 19.2 mmol, 1.3 equivalents) was added dropwise to a solution of bifuran (2 g, 14.9 mmol) in dry THF (100 mL) at −78° C. under N2. The mixture was allowed to come to room temperature and stirred for 1 h. To the white suspension was added dropwise Bu3SnCl (4 mL, 14.9 mmol) at 0° C. and the reaction was allowed to reach room temperature and stirred for 2 h. The mixture was extracted with hexane, dried (MgSO4) and evaporated. Seperation by chromatography using bacified silica (Et3N) and hexane gave 1 (3.8 g, 60% yield) as a colorless oil. 1H NMR (300 MHz, CDCl3): δ 0.85-0.91 (t, J=7.3 Hz, 9H), 1.03-1.13 (m, 6H), 1.26-1.39 (m, 6H), 1.48-1.63 (m, 6H), 6.40-6.42 (m, 1H), 6.50 (d, J=3.3 Hz, 1H), 6.57 (dd, J=3.3, 6.0 Hz, 2H), 7.34 (dd, J=0.7, 1.8 Hz, 1H) ppm. 13C NMR (300 MHz, CDCl3): δ 10.2, 13.7, 27.2, 28.9, 104.6, 105.0, 111.3, 123.0, 141.4, 147.5, 151.0, 160.9 ppm

Workup

  1. customto come to room temperature
  2. customto reach room temperature
  3. stirringstirred for 2 h
  4. extractionThe mixture was extracted with hexane
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customSeperation by chromatography

Sources & evidence

ORD record
ord-a051b7894e01484194bf93ef5ed7f214
Source dataset
uspto-grants-2014_06
Patent number
US08759550B2

Reaction notes

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