反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
実験手順: A mixture of homovanillyl alcohol (100 mmol, 17.0 g), benzyl bromide (105 mmol, 18.33 g) and 5M aqueous NaOH (24 mL) in ethanol (200 mL) was refluxed for 6 h. The organic solvent was evaporated in vacuo. The residue was partitioned between brine (200 mL) and diethyl ether (200 mL). The aqueous layer was separated from the organic layer and extracted again with ether. The combined organic layers were dried over MgSO4 and the solvent was evaporated in vacuo. Purification by dry-column chromatography with mixtures of ethyl acetate-hexanes (1:4, 1:3, v/v) yielded 20.66 g (80% yield) of (DC-61) as pale yellow oil. Rf 0.25 (EtOAc-hexanes, 1:1, v/v); 1H-NMR (300 MHz, CDCl3) δ 7.44-7.25 (m, 5H, Ar), 6.84-6.67 (m, 3H, Ar), 5.12 (s, 2H, PhCH2O), 3.88 (s, 3H, CH3O), 3.81 (t, 2H, CH2CH2OH), 2.79 (t, 2H, CH2CH2OH), 1.54 (s, 1H, OH); 13C-NMR (75 MHz, CDCl3, APT) δ 149.63 (+), 146.75 (+), 137.21 (+), 131.60 (+), 128.43 (−), 127.70 (−), 127.17 (−), 120.84 (−), 114.25 (−), 112.74 (−), 71.07 (+), 63.58 (+), 55.90 (−), 38.67 (+).
was refluxed for 6 h
The organic solvent was evaporated in vacuo
The residue was partitioned between brine (200 mL) and diethyl ether (200 mL)
The aqueous layer was separated from the organic layer
extracted again with ether
The combined organic layers were dried over MgSO4
the solvent was evaporated in vacuo
Purification by dry-column chromatography with mixtures of ethyl acetate-hexanes (1:4, 1:3
v/v) yielded 20.66 g (80% yield) of (DC-61) as pale yellow oil
ソース ID: ord-7aaadf052c854f63b88a58a0691e555f