{1-[4-(Benzyloxy)phenyl]ethenyl}(tributyl)stannane → 2,3-Di(4-benzyloxy-phenyl)-1,3-butadiene

HRID 351434

Reaction equation

C([Sn](CCCC)(CCCC)[C:6]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:10][CH:9]=1)=[CH2:7])CCC>CN(C=O)C.C(OCC)(=O)C.Cl[Cu]>[CH2:15]([O:14][C:11]1[CH:12]=[CH:13][C:8]([C:6]([C:6]([C:8]2[CH:9]=[CH:10][C:11]([O:14][CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[CH:12][CH:13]=2)=[CH2:7])=[CH2:7])=[CH:9][CH:10]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a cooled solution of tributyl-[1-(4-benzyloxy-phenyl)-vinyl]-stannane (26.2 g, 52.6 mmol) in DMF (180 mL) at 0° C. was added CuCl (8.6 g, 87.7 mmol) and CuCl2 (1.00 g, 8.13 mmol), which was then stirred at 25° C. for 2 h. The reaction mixture was then diluted with ethyl acetate (500 mL) and washed with brine (3×300 mL). The reaction mixture was then dried over MgSO4 and purified by SiO2 (20% ethyl acetate/hexane) to yield 2,3-di(4-benzyloxy-phenyl)-1,3-butadiene.

Workup

washwashed with brine (3×300 mL)
dry with materialThe reaction mixture was then dried over MgSO4
custompurified by SiO2 (20% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-7d8fd34e7b16494ab4b6b84115eb2720
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07183445B2

Linked notes

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