Benzene → Methyl 2-methoxy-5-{1-[4-methoxy-3-(methoxycarbonyl)phenyl]hept-1-en-1-yl}benzoate

Temperature

0 °C

n-Hexyltriphenylphosphonium bromide (0.427 g, 1 mmol) was dried by azeotropic distillation from a benzene solution and then stirred in dry THF (10 mL) under nitrogen atmosphere. Sodium bis(trimethylsilyl)amide (1 M in THF, 1 mL, 1 mmol) was added and the ylide produced was stirred under nitrogen at 0° C. for 30 min. Intermediate 35 (0.276 g, 0.77 mmol) was added as a solution in THF (10 mL) under nitrogen. The mixture was stirred at rt overnight and partitioned between 1 N HCl (100 mL) and ethyl acetate (100 mL). The organic layer was dried over sodium sulfate, and evaporated to afford an oil which was chromatographed on SiO2 (230-400 mesh, 50 g), eluting with hexanes/ethyl acetate (4:1) to give the product (36) (0.15 g, 46%) as an oil: 1H NMR (CDCl3, 300 MHz) δ 7.63 (d, J=2.3 Hz, 1H), 7.56 (d, J=2.2 Hz, 1H), 7.20 (dt, J=2.3 Hz, 1H), 6.94 (d, J=8.6 Hz, 1H), 6.82 (d, J=8.7H, 1H), 5.96 (t, J=7.5 Hz, 1H), 3.90 (s, 3H), 3.84 (s, 3H), 3.83 (s, 6H), 2.05 (q, J=7.3 Hz, 2H), 1.39 (t, J=7.2 Hz, 2H), 1.22 (m, J=1.9 Hz, 2H), 0.83 (t, J=6.7 Hz, 3H); IR (neat) 2927, 2853, 1732, 1606, 1500, 1435, 1263 cm−1. Anal. (C25H30O6) C, H.

1. customthe ylide produced
2. stirringThe mixture was stirred at rt overnight
3. custompartitioned between 1 N HCl (100 mL) and ethyl acetate (100 mL)
4. dry with materialThe organic layer was dried over sodium sulfate
5. customevaporated
6. customto afford an oil which
7. customwas chromatographed on SiO2 (230-400 mesh, 50 g)
8. washeluting with hexanes/ethyl acetate (4:1)

ORD record

ord-cdd3348516b04c96bcea16df332c51de

Source dataset

uspto-grants-2003_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06569897B1