Triethyl 2-phosphonopropionate → HCID 68534712, compound

HRID 1992971Notes

Reaction equation

HRID 1992971 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.[CH3:29][CH2:30][O:31][C:32]([CH:34](P(OCC)(OCC)=O)[CH3:35])=[O:33].[Li]CCCC>C1COCC1>[CH2:30]([O:31][C:32](=[O:33])[C:34]([CH3:35])=[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)[CH3:29]

Participants

5

Reactant 3

HCID 107155Triethyl 2-phosphonopropionateHCID 860871594-[(6-Methoxy-3-methyl-2-phenyl-1-naphthyl)oxy]benzaldehydeHCID 178418339Butyllithium

Product 1

HCID 68534712HCID 68534712, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

As described above, 4-(6-Methoxy-3-methyl-2-phenyl-naphthalen-1-yloxy)-benzaldehyde (8) (0.21 g, 0.570 mmol), triethyl 2-phosphonopropionate (0.183 mL, 0.855 mmol), 1.6 M nBuLi (0.57 mL, 0.912 mmol) in dry THF (8 mL) afforded 0.2 g (78%) of the title compound (219) as oil. 1H NMR (400 MHz, d-CDCl3): δ 1.31 (t, J=7.1 Hz, 3H), 2.04 (s, 3H), 2.24 (s, 3H), 3.93 (s, 3H), 4.20-4.25 (m, 2H), 6.59 (d, J=8.8 Hz, 2H), 7.03-7.06 (m, 1H), 7.11-7.16 (m, 5H), 7.21-7.25 (m, 3H), 7.55 (d, J=9.7 Hz, 2H), 7.75 (d, J=9.1 Hz, 1H).

Sources & evidence

ORD record
ord-72d2d67239ef4537b767af168ebcff6e
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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