Tetrahydrofuran → Methyl 2'-methyl-6'-propylbiphenyl-3-carboxylate

To a suspension (21 mL) of ethyltriphenylphosphonium bromide (1.55 g, 4.13 mmol) in tetrahydrofuran was added sodium hydride (0.14 g, 3.58 mmol) at room temperature with stirring, and the mixture was stirred at the same temperature for 20 min. A solution (20 mL) of methyl 2′-formyl-6′-methylbiphenyl-3-carboxylate (0.70 g, 2.75 mmol) in tetrahydrofuran was added and the mixture was stirred at 70° C. for 3 hrs. The reaction mixture was cooled, diluted with ethyl acetate, washed with water and saturated brine, dried, and concentrated under reduced pressure. Then a mixture of the obtained residue, 10% Pd carbon (0.1 g) and methanol (14 mL) was stirred under a hydrogen atmosphere for 2 hrs. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-hexane/ethyl acetate=4/1) to give the title compound (0.63 g, yield 85%) as a colorless oil.

1. stirringthe mixture was stirred at the same temperature for 20 min
2. stirringthe mixture was stirred at 70° C. for 3 hrs
3. temperatureThe reaction mixture was cooled
4. washwashed with water and saturated brine
5. customdried
6. concentrationconcentrated under reduced pressure
7. additionThen a mixture of the obtained residue, 10% Pd carbon (0.1 g) and methanol (14 mL)
8. stirringwas stirred under a hydrogen atmosphere for 2 hrs
9. filtrationThe catalyst was filtered off
10. concentrationthe filtrate was concentrated under reduced pressure
11. customThe residue was purified by silica gel column chromatography (hexane-hexane/ethyl acetate=4/1)

ORD record

ord-2185b5a2dca341819d941281aea6f4f0

Source dataset

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07960369B2