(Z)-2-(3,4-dimethoxyphenyl)-3-(4-hydroxyphenyl)acrylonitrile → 4-[(Z)-2-cyano-2-(3,4-dimethoxy-phenyl)-vinyl]-phenyl ethyl succinate

HRID 2222363Notes

Reaction equation

HRID 2222363 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[C:11](=[CH:14]/[C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)/[C:12]#[N:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[Cl-].[CH2:23]([O:25][C:26](=[O:32])[CH2:27][CH2:28][C:29](O)=[O:30])[CH3:24]>N1C=CC=CC=1>[C:29]([O:21][C:18]1[CH:17]=[CH:16][C:15](/[CH:14]=[C:11](\[C:12]#[N:13])/[C:5]2[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)=[CH:20][CH:19]=1)(=[O:30])[CH2:28][CH2:27][C:26]([O:25][CH2:23][CH3:24])=[O:32]

Participants

4

Reactant 2

HCID 10446442(Z)-2-(3,4-dimethoxyphenyl)-3-(4-hydroxyphenyl)acrylonitrileHCID 77519041Succinic acid monoethyl ester monochloride

Product 1

HCID 100471094-[(Z)-2-cyano-2-(3,4-dimethoxy-phenyl)-vinyl]-phenyl ethyl succinateYield 90%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Compound 1 (50 mg) and succinic acid monoethyl ester chloride (51 μL) were dissolved in pyridine (1 mL), followed by stirring for a whole day and night. After completion of reaction, the resultant reaction mixture was concentrated to dryness under reduced pressure, followed by purification by means of silica gel chromatography employing a chloroform/methanol system, to thereby produce the target product (73 mg, yield: 90%).

Workup

  1. customAfter completion of reaction
  2. customthe resultant reaction mixture
  3. concentrationwas concentrated to dryness under reduced pressure
  4. customfollowed by purification by means of silica gel chromatography

Sources & evidence

ORD record
ord-4d29862f1a6a4a93b96a61d3ba7b81fd
Source dataset
uspto-grants-2008_05
Patent number
US07371773B2

Reaction notes

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