Реакция #587156

Уравнение реакции

LiCl

2,6-Diformyl-4-bromophenol

1-dodecene

NaHCO3

→

title compound

Выход 51.0%

2,6-Diformyl-4-(dodecen-1-yl)phenol

Выход 51.0%

Условия реакции

Обработка

1. 1
   Другоеdegassed anhydrous dimethylformamide (DMF)
2. 2
   ДругоеThe mixture was sparged with argon for 10 min
3. 3
   Другоеsealed in a pressure vial which
4. 4
   ДругоеThe crude reaction mixture
5. 5
   Другоеwas partitioned between CH2Cl2 and 0.1 M HCl solution
6. 6
   ПромывкаThe organic layer was washed with 0.1 M HCl (2×), brine (2×), and saturated aqueous NaHCO3 (2×)
7. 7
   Сушкаdried over MgSO4
8. 8
   Концентрированиеconcentrated under reduced pressure
9. 9
   ДругоеThe dark yellow oil was purified by column chromatography on silica gel (25% hexanes in Et2O)

Методика

2,6-Diformyl-4-bromophenol (1.00 g, 4.37 mmol), 1-dodecene (4.8 mL, 21.7 mmol), 1.40 g tetrabutylammonium bromide (4.34 mmol), 0.50 g NaHCO3 (5.95 mmol), 1.00 g LiCl (23.6 mmol) and 0.100 g palladium diacetate (Pd(OAc)2) (0.45 mmol) were combined in 30 mL degassed anhydrous dimethylformamide (DMF). The mixture was sparged with argon for 10 min and then sealed in a pressure vial which was warmed to 82° C. and held for 40 h. The crude reaction mixture was partitioned between CH2Cl2 and 0.1 M HCl solution. The organic layer was washed with 0.1 M HCl (2×), brine (2×), and saturated aqueous NaHCO3 (2×), dried over MgSO4 and concentrated under reduced pressure. The dark yellow oil was purified by column chromatography on silica gel (25% hexanes in Et2O) to give 0.700 g (51%) of the title compound as primarily the Z isomer.

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