Methyl diethylphosphonoacetate → HCID 69203667, compound

HRID 971029Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([C:13]2[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[C:15]([O:21][CH3:22])[CH:14]=2)=O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH3:23][O:24][C:25](=[O:35])[CH2:26]P(OCC)(OCC)=O.[CH3:36][Si]([N-][Si](C)(C)C)(C)C.[Li+].COC1C=C(C(C2C=CC=C(OC)C=2)=CC#N)C=C(OC)C=1>>[CH2:23]([O:24][C:25](=[O:35])[CH:26]=[C:11]([C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)[C:13]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[C:15]([O:21][CH3:22])[CH:14]=1)[CH3:36]

Participants

Reactant 4

HCID 66113Methyl diethylphosphonoacetate

HCID 2733832Lithium Hexamethyldisilazide

HCID 21584591(3,4-Dimethoxyphenyl)(3,5-dimethoxyphenyl)methanone

HCID 692052993-(3,5-Dimethoxy-phenyl)-3-(3-methoxy-phenyl)-acrylonitrile

Product 1

HCID 69203667HCID 69203667, compoundYield 43%

Procedure

(3,4-Dimethoxyphenyl)-(3,5-dimethoxyphenyl)methanone (1.50 g, 4.95 mmol), (diethoxyphosphoryl)acetic acid methyl ester (2.29 g, 9.90 mmol), and lithium bis(trimethylsilyl)amide (1.0 M solution in THF, 9.90 ml, 9.90 mmol) were treated in the same manner as described above for the synthesis of 3-(3,5-dimethoxy-phenyl)-3-(3-methoxy-phenyl)-acrylonitrile. The crude yellowish oil was purified via preparative HPLC to give 3-(3,4-dimethoxy-phenyl)-3-(3,5-dimethoxy-phenyl)-acrylic acid ethyl ester as a light yellow oil (0.79 g, 43%): 1HNMR (CDCl3) δ 6.89-6.72 (m, 2H, Ar), 6.48-6.45 (m, 4H, Ar), 6.28 (s, 1H, double bond proton), 4.09 (q, J=7 Hz, 2H, CH2CH3), 3.92 (s, 3H, OCH3), 3.82 (s, 3H, OCH3), 3.75 (s, 6H, 2OCH3), 1.16 (t, J=7 Hz, 3H, CH2CH3). The product was carried over to the next step.

Workup

customThe crude yellowish oil was purified via preparative HPLC

Sources & evidence

ORD record: ord-38c421952ca841e7b99f7139541bb9e7
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07312241B2

Reaction notes

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