Diethyl (cyanomethyl)phosphonate → HCID 69205834, compound

HRID 971034Notes

Reaction equation

HRID 971034 reaction equation
[Si:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([C:17]2[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[C:19]([O:25][CH3:26])[CH:18]=2)=O)=[CH:11][C:10]=1[O:27][CH3:28])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(OP([CH2:37][C:38]#[N:39])(=O)OCC)C.C[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>C1COCC1>[C:4]([Si:1]([CH3:3])([CH3:2])[O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([C:17]2[CH:18]=[C:19]([O:25][CH3:26])[CH:20]=[C:21]([O:23][CH3:24])[CH:22]=2)=[CH:37][C:38]#[N:39])=[CH:11][C:10]=1[O:27][CH3:28])([CH3:6])([CH3:5])[CH3:7]

Participants

6

Reactant 4

HCID 75676Diethyl (cyanomethyl)phosphonateHCID 2733832Lithium HexamethyldisilazideHCID 69203625HCID 69203625, compoundHCID 692052993-(3,5-Dimethoxy-phenyl)-3-(3-methoxy-phenyl)-acrylonitrile

Product 1

HCID 69205834HCID 69205834, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

[4-(tert-Butyldimethylsilanyloxy)-3-methoxyphenyl]-(3,5-dimethoxyphenyl)methanone (3.64 g, 9.04 mmol), cyanomethylphosphonic acid diethyl ester (2.85 ml, 18.08 mmol) in anhydrous THF (10 ml), and lithium bis(trimethylsilyl)amide (1.0 M solution in THF, 18.08 ml, 18.08 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 was purified via flash column chromatography (5% EtOAc in hexane gradient to 20% EtOAc in hexane in about 30 min.) to give 3-[4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-phenyl]-3-(3,5-dimethoxy-phenyl)-acrylonitrile as a white solid (3.00 g, 78%). The product was carried over to the next step without further purification.

Workup

  1. customThe crude was purified via flash column chromatography (5% EtOAc in hexane gradient to 20% EtOAc in hexane in about 30 min.)

Sources & evidence

ORD record
ord-3b276ede4475481aa5939a83d2d3d849
Source dataset
uspto-grants-2007_12
Patent number
US07312241B2

Reaction notes

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