Water → HCID 9863370, compound

HRID 2378312Notes

Reaction equation

HRID 2378312 reaction equation
C(OP([CH2:9][C:10]#[N:11])(=O)OCC)C.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH2:22]([O:24][C:25]1[CH:26]=[C:27]([C:33]([C:35]2[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[C:37]([O:43][CH2:44][CH3:45])[CH:36]=2)=O)[CH:28]=[CH:29][C:30]=1[O:31][CH3:32])[CH3:23].O>C1COCC1>[CH2:44]([O:43][C:37]1[CH:36]=[C:35]([C:33]([C:27]2[CH:28]=[CH:29][C:30]([O:31][CH3:32])=[C:25]([O:24][CH2:22][CH3:23])[CH:26]=2)=[CH:9][C:10]#[N:11])[CH:40]=[CH:39][C:38]=1[O:41][CH3:42])[CH3:45]

Participants

6

Reactant 4

HCID 962WaterHCID 75676Diethyl (cyanomethyl)phosphonateHCID 2733832Lithium HexamethyldisilazideHCID 69205642Bis(3-ethoxy-4-methoxyphenyl)methanone

Product 1

HCID 9863370HCID 9863370, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of cyanomethylphosphonic acid diethyl ester (7.0 mL, 44.4 mmol) in anhydrous THF (20 mL) was added lithium bis(trimethylsilyl)amide (1.0 M solution in THF, 44.4 mL, 44.4 mmol) at 0° C. and stirred for 30 min followed by addition of bis-(3-ethoxy-4-methoxy-phenyl)-methanone (7.34 g, 22.2 mmol) and refluxed for 3 h. The reaction mixture was poured into water (100 mL), extracted with CH2Cl2 (2×100 mL). The combined organic phases were washed with brine (100 mL), dried over MgSO4, and purified via flash column chromatography (EtOAc/Hexane) to give 3,3-bis-(3-ethoxy-4-methoxy-phenyl)-acrylonitrile as a white solid (3.92 g, 50% yield): 1H NMR (DMSO-d6) δ 1.31 (t, J=7 Hz, 6H, 2CH2CH3), 3.79 (s, 3H, OCH3), 3.83 (s, 3H, OCH3), 3.94-4.04 (two q, J=7 Hz, 4H, 2CH2CH3), 6.11 (s, 1H, CH), 6.77-7.09 (m, 6H, Ar); 13C NMR (DMSO-d6) δ 14.6, 14.6, 55.5, 55.5, 63.8, 92.6, 111.3, 111.5, 112.3, 113.8, 118.9, 122.3, 122.4, 129.3, 130.6, 147.3, 147.8, 150.1, 151.0, 161.4; Anal. Calcd for C21H23NO4: C, 71.37; H, 6.56; N, 3.96. Found: C, 71.42; H, 6.42; N, 3.97.

Workup

  1. temperaturerefluxed for 3 h
  2. extractionextracted with CH2Cl2 (2×100 mL)
  3. washThe combined organic phases were washed with brine (100 mL)
  4. dry with materialdried over MgSO4
  5. custompurified via flash column chromatography (EtOAc/Hexane)

Sources & evidence

ORD record
ord-26245d9007964b37bf677f2254d4e23c
Source dataset
uspto-grants-2008_12
Patent number
US07470723B2

Reaction notes

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