Diethyl (cyanomethyl)phosphonate → HCID 10333082, compound

HRID 2378232Notes

Reaction equation

HRID 2378232 reaction equation
COC1C=C(C(C2C=CC=C(OC)C=2)=O)C=CC=1.C(OP(CC#N)(=O)OCC)C.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH3:40][O:41][C:42]1[CH:43]=[C:44]([C:50]([C:54]2[CH:59]=[CH:58][CH:57]=[C:56]([O:60][CH3:61])[CH:55]=2)=[CH:51][C:52]#[N:53])[CH:45]=[C:46](OC)[CH:47]=1>C1COCC1>[CH3:61][O:60][C:56]1[CH:55]=[C:54]([C:50]([C:44]2[CH:45]=[CH:46][CH:47]=[C:42]([O:41][CH3:40])[CH:43]=2)=[CH:51][C:52]#[N:53])[CH:59]=[CH:58][CH:57]=1

Participants

6

Reactant 4

HCID 75676Diethyl (cyanomethyl)phosphonateHCID 2733832Lithium HexamethyldisilazideHCID 12548810Bis(3-methoxyphenyl)methanoneHCID 692052993-(3,5-Dimethoxy-phenyl)-3-(3-methoxy-phenyl)-acrylonitrile

Product 1

HCID 10333082HCID 10333082, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Bis-(3-methoxyphenyl)methanone (1.23 g, 5.08 mmol), cyanomethylphosphonic acid diethyl ester (1.60 ml, 10.15 mmol) in anhydrous THF (10 ml), and lithium bis(trimethylsilyl)amide (1.0 M solution in THF, 10.15 ml, 10.15 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 (10% EtOAc in hexane gradient to 25% EtOAc in hexane) to give 3,3-bis-(3=methoxy-phenyl)-acrylonitrile as a clear colorless oil (0.76 g, 56%): 1HNMR (DMSO-d6) δ 7.47-7.30 (two triplets, 2H, Ar), 7.12-7.04 (m, 2H, Ar), 6.98-6.82 (m, 4H, Ar), 6.38(s, 1H, double bond proton), 3.78 (s, 3H, OCH3), 3.76 (s, 3H, OCH3); 13C NMR (CDCl3) δ 163.0, 159.8, 159.6, 140.3, 138.3, 129.8, 129.7, 122.1, 121.1, 117.9, 116.1, 115.9, 115.0, 114.4, 95.3, 55.5; Anal. Calcd. For C17H15NO2: C, 76.96; H, 5.70; N, 5.28. Found: C, 76.65; H, 5.72; N, 5.15.

Workup

  1. customThe crude was purified via flash column chromatography (10% EtOAc in hexane gradient to 25% EtOAc in hexane)
  2. customto give 3,3-bis-(3=methoxy-phenyl)-acrylonitrile as a clear colorless oil (0.76 g, 56%)

Sources & evidence

ORD record
ord-94310d98445a4da8a02b37d0c2d15e4c
Source dataset
uspto-grants-2008_12
Patent number
US07470723B2

Reaction notes

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