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

온도

82 °C

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 LiCI (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 CH2CI2 and 0.1 M HCI solution. The organic layer was washed with 0.1 M HCI (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.

1. customdegassed anhydrous dimethylformamide (DMF)
2. customThe mixture was sparged with argon for 10 min
3. customsealed in a pressure vial which
4. customThe crude reaction mixture
5. customwas partitioned between CH2CI2 and 0.1 M HCI solution
6. washThe organic layer was washed with 0.1 M HCI (2×), brine (2×), and saturated aqueous NaHCO3 (2×)
7. dry with materialdried over MgSO4
8. concentrationconcentrated under reduced pressure
9. customThe dark yellow oil was purified by column chromatography on silica gel (25% hexanes in Et2O)

ORD 기록

ord-df6876f6aec947b690b736cbf5e1fe23

출처 데이터셋

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07563890B2