Ethyl 2-(diethoxyphosphoryl)-3-methylbutanoate → 2-[4-(6-Methoxy-3-methyl-2-phenyl-naphthalen-1-yloxy)-benzylidene]-3-methyl-butyric acid ethyl ester

Participants

Reaction Steps

Using the procedure described in Example 31 (Step 3), reaction of 4-(6-Methoxy-3-methyl-2-phenyl-naphthalen-1-yloxy)-benzaldehyde (8) (0.507 g, 1.38 mmol), 2-(diethoxy-phosphoryl)-3-methyl-butyric acid ethyl ester (1.1 g, 4.13 mmol) and 1.6 M nBuLi (2.8 mL, 4.41 mmol) in dry THF (14 mL) afforded 2 isomeric products (222) as oils. Yield: (222-1) Isomer (1) 0.177 (27%); (222-2) Isomer (2) 0.195 g (30%). Isomer (1): 1H NMR (400 MHz, d-CDCl3): δ 1.20 (d, J=6.9 Hz, 6H), 1.32 (t, J=7.1 Hz, 3H), 2.24 (s, 3H), 3.06-3.10 (m, 1H), 3.94 (s, 3H), 4.20-4.25 (m, 2H), 6.58 (d, J=8.8 Hz, 2H), 7.03-7.07 (m, 3H), 7.12-7.14 (m, 3H), 7.22-7.26 (m, 3H), 7.39 (s, 1H), 7.56 (s, 1H), 7.78 (d, J=9.1 Hz, 1H).

Provenance & Evidence