Реакция #339953

Уравнение реакции

5-iodo-1,2,3-trimethoxybenzene

2,3-dihydrofuran

KOAc

→

title compound 287

Выход 43.1%

2-(3,4,5-Trimethoxy-phenyl)-2,3-dihydro-furan

Выход 43.1%

Растворители

AcOEt

water

DMF

Условия реакции

Обработка

1. 1
   ДругоеAfter separation
2. 2
   Промывкаthe organic layer was washed with brine
3. 3
   Сушкаdried over anhydrous Na2SO4
4. 4
   Фильтрацияfiltered
5. 5
   Концентрированиеconcentrated
6. 6
   ДругоеThe crude residue was then purified by flash chromatography on silica gel (AcOEt/Hexane: 20/80)

Методика

To a solution of 5-iodo-1,2,3-trimethoxybenzene (900 mg, 3.06 mmol) and 2,3-dihydrofuran (1.16 mL, 15.3 mmol) in dry DMF (8 mL) were added PPh3 (20 mg, 0.077 mmol), KOAc (901 mg, 9.18 mmol), n-Bu4NCl (850 mg, 3.06 mmol) and Pd(OAc)2 (17 mg, 0.077 mmol). The reaction mixture was stirred 18 h at 80° C. The reaction mixture was diluted with AcOEt and water. After separation, the organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated. The crude residue was then purified by flash chromatography on silica gel (AcOEt/Hexane: 20/80) to afford the title compound 287 (311 mg, 1.32 mmol, 43% yield). 1H NMR: (300 MHz, CDCl3) δ (ppm): 6.59 (s, 2H), 6.45 (m, 1H), 5.45 (dd, J=10.5, 8.4 Hz, 1H), 4.97 (m, 1H), 3.87 (s, 6H), 3.84 (s, 3H), 3.06 (m, 1H), 2.62 (m, 1H).

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