Potassium Carbonate → ethyl 7-[4-[(Z)-2-cyano-2-(3,4-dimethoxy-phenyl)-vinyl]-phenoxy]-heptanoate

HRID 2222379Notes

Reaction equation

HRID 2222379 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].C(=O)([O-])[O-].[K+].[K+].Br[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36]>CS(C)=O>[C:12](/[C:11](/[C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)=[CH:14]\[C:15]1[CH:16]=[CH:17][C:18]([O:21][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])=[CH:19][CH:20]=1)#[N:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 122490Ethyl 7-bromoheptanoateHCID 10446442(Z)-2-(3,4-dimethoxyphenyl)-3-(4-hydroxyphenyl)acrylonitrile

Product 1

HCID 9980517ethyl 7-[4-[(Z)-2-cyano-2-(3,4-dimethoxy-phenyl)-vinyl]-phenoxy]-heptanoateYield 72%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Compound 1 (200 mg) was dissolved in dimethyl sulfoxide, and anhydrous potassium carbonate was added to the resultant solution, followed by stirring at room temperature for one hour. Thereafter, ethyl 7-bromoheptanoate (169 mg) was added to the resultant mixture, and the mixture was stirred. The potassium carbonate was separated through filtration, and the resultant filtrate was poured into ice water. Hydrochloric acid was added to the resultant mixture so as to adjust the pH to 3, and then the mixture was subjected to extraction with chloroform twice. The resultant chloroform layer was washed with brine, and then dried over anhydrous sodium sulfate. The sodium sulfate was separated through filtration, and the resultant filtrate was concentrated to dryness under reduced pressure, followed by recrystallization, to thereby produce the target product (223 mg, yield: 72%).

Workup

  1. stirringthe mixture was stirred
  2. customThe potassium carbonate was separated through filtration
  3. additionthe resultant filtrate was poured into ice water
  4. additionHydrochloric acid was added to the resultant mixture so as
  5. extractionthe mixture was subjected to extraction with chloroform twice
  6. washThe resultant chloroform layer was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe sodium sulfate was separated through filtration
  9. concentrationthe resultant filtrate was concentrated to dryness under reduced pressure
  10. customfollowed by recrystallization

Sources & evidence

ORD record
ord-88892843be8d4fa7bff6835023f0a465
Source dataset
uspto-grants-2008_05
Patent number
US07371773B2

Reaction notes

Loading…