| Ca. 81.2% |
With aluminum (III) chloride; In 1,2-dichloro-ethane; at -20 - -10℃;Large scale; |
10.70 kg (80.4 mol, 1.0 eq) of aluminum trichloride was added to 60.00 kg of 1,2-dichloroethane at -20 to -10 C.14.00 kg (80.4 mol, 1.0 eq) of compound 5 was added with stirring.After stirring uniformly, 16.46 kg (96.5 mol, 1.2 eq) of Compound 7 was added at -20 to -10 C, and the reaction was kept for 1 to 2 hours.After the reaction, the reaction solution was transferred to 90.00 kg of purified water, the pH was adjusted to 2 with dilute hydrochloric acid, and the organic phase was added and washed with 25.00 kg of purified water twice.The organic phase was washed with 45.00 kg of a saturated aqueous solution of sodium chloride and dried over 1.40 g of anhydrous sodium sulfate.The organic phase was concentrated under reduced pressure at 55 C.20.11 kg (65.0 mol) of compound 8 was obtained.The yield was about 81.2%. |
| 71% |
With aluminum (III) chloride; In dichloromethane; at 20℃; for 24h;Inert atmosphere; |
General procedure: To a solution of compound 2 (5.4 g, 24.83 mmol)and 4-methoxybenzoyl chloride (4.4 mL, 32.28 mmol) in DCM (50 mL) was added AlCl3(3.3 g, 24.83 mmol). The mixture was stirred at room temperature for 24hours and was quenchedwith ice water (50 mL). The reaction mixture was extractedwith DCM (350 mL). The organic phase was dried over Na2SO4,filtered and concentrated to give the crude product, which was purified byflash chromatography [PE/EA=10:1] to give 3 (6.9 g, 78.9%) as a yellowsolid. |
| 64% |
|
2-butylbenzofuran (400 mg, 0.405 mL, 2.30 mmol) was weighed out into a dry RBF (25 mL) containing a SB. The material was diluted in CS2 (6.0 mL), capped and a N2 balloon attached. The mixture was stirred and cooled in an ice bath (30 min). Next, 4-methoxybenzoyl chloride (0.404 mL, 2.98 mmol) was added followed by dropwise addition of tin (IV) chloride (0.370 mL, 2.98 mmol). The contents were stirred (3 h) at 0 C and slowly warmed to RT and stirred (3 d). The reaction mixture was diluted with ¾0 and extracted with EtOAc (4 x 12 mL). The combined organic layer was washed with HC1 (0.5 N), H20, sat. NaHC03, and brine. The organic layer was dried (Na2S0 ), filtered and concentrated in vacuo. The crude material was purified by column chromatography on Si02 (100% hexanes to 5% ethyl acetate in hexanes) to give 86 (0.455 g, 1.48 mmol, 64%) as a clear oil. -NMR (400 MHz) CDC13: 7.87-7.85 (d, 2 H), 7.49-7.47 (d, 1 H), 7.38-7.36 (d, 1 H), 7.28-7.25 (m, 1 H), 7.20-7.16 (m, 1 H), 6.97- 6.95 (d, 2 H), 3.88 (s, 3 H), 2.95-2.91 (t, 2 H) 1.79-1.75 (m, 2 H), 1.40-1.34 (m, 2 H), 0.92- 0.88 (t, 3 H); .3C-NMR (100 MHz) CDC13: 190.5, 164.6, 163.4, 153.6, 131.9, 131.7, 127.2, 124.1, 123.3, 121.2, 1 16.8, 113.7, 1 11.9, 55.5, 30.2, 27.8, 22.4, 13.7. |
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