HCID 68522041, compound → 3-(4-Iodophenyl)-4-cyano-5-ethyl-thiophene-2-carboxylic acid ethyl ester

HRID 1990078Notes

Reaction equation

HRID 1990078 reaction equation
C([Zn][CH2:4][CH3:5])C.[CH2:6]([O:8][C:9]([C:11]1[S:12][C:13](S(C)(=O)=O)=[C:14]([C:23]#[N:24])[C:15]=1[C:16]1[CH:21]=[CH:20][C:19]([I:22])=[CH:18][CH:17]=1)=[O:10])[CH3:7]>C(Cl)Cl>[CH2:6]([O:8][C:9]([C:11]1[S:12][C:13]([CH2:4][CH3:5])=[C:14]([C:23]#[N:24])[C:15]=1[C:16]1[CH:21]=[CH:20][C:19]([I:22])=[CH:18][CH:17]=1)=[O:10])[CH3:7]

Participants

4

Reactant 2

HCID 68522041HCID 68522041, compoundHCID 178418750HCID 178418750, compound

Product 1

HCID 685221773-(4-Iodophenyl)-4-cyano-5-ethyl-thiophene-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add dropwise diethylzinc (1.0M in hexanes, 16 mmol) to a solution of 3-(4-iodophenyl)-4-cyano-5-methanesulfonyl-thiophene-2-carboxylic acid ethyl ester (2.78 mmol) in 15 mL of anhydrous CH2Cl2 and stir under nitrogen at room temperature for 5 days. Cool to 0° C. and carefully quench with ice followed by 10 mL of saturated NH4Cl. Filter the mixture through Celite and rinse the filter pad with 100 mL of CH2Cl2. Wash the combined organic layers with brine (1×20 mL), dry over Na2SO4, filter, and evaporate. Chromatograph (hexane:ethyl acetate 3:1) over silca gel to provide the title compound: MS (ES+, m/e): 412 (M+1).

Workup

  1. temperatureCool to 0° C.
  2. customcarefully quench with ice
  3. filtrationFilter the mixture through Celite
  4. washrinse the filter pad with 100 mL of CH2Cl2
  5. washWash the combined organic layers with brine (1×20 mL)
  6. dry with materialdry over Na2SO4
  7. filtrationfilter
  8. customevaporate

Sources & evidence

ORD record
ord-93b78a81ab32493a8351cd11a88d4a44
Source dataset
uspto-grants-2010_01
Patent number
US07642361B2

Reaction notes

Loading…