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

HRID 1992973Notes

Reaction equation

HRID 1992973 reaction equation
[CH3:1][C:2]1[C:3]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:4]([O:14][C:15]2[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=2)[C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:12][CH3:13])=[CH:7][CH:6]=2.[CH2:29]([O:31][C:32](=[O:45])[CH:33](P(OCC)(OCC)=O)[CH:34]([CH3:36])[CH3:35])[CH3:30].[Li]CCCC>C1COCC1>[CH2:29]([O:31][C:32](=[O:45])[C:33](=[CH:19][C:18]1[CH:17]=[CH:16][C:15]([O:14][C:4]2[C:5]3[C:10](=[CH:9][C:8]([O:12][CH3:13])=[CH:7][CH:6]=3)[CH:11]=[C:2]([CH3:1])[C:3]=2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:22][CH:21]=1)[CH:34]([CH3:35])[CH3:36])[CH3:30]

Participants

5

Reactant 3

HCID 11777661Ethyl 2-(diethoxyphosphoryl)-3-methylbutanoateHCID 860871594-[(6-Methoxy-3-methyl-2-phenyl-1-naphthyl)oxy]benzaldehydeHCID 178418339Butyllithium

Product 1

HCID 685360972-[4-(6-Methoxy-3-methyl-2-phenyl-naphthalen-1-yloxy)-benzylidene]-3-methyl-butyric acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Sources & evidence

ORD record
ord-59387ac7738f4627aae0b436d835576e
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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