HCID 58873061, compound → Ethyl 4-cyano-3-[4-(1,1-dimethylethyl)phenyl]-5-ethyl-2-thiophenecarboxylate

HRID 1990092Notes

Reaction equation

HRID 1990092 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:26]#[N:27])[C:15]=1[C:16]1[CH:21]=[CH:20][C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])=[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:26]#[N:27])[C:15]=1[C:16]1[CH:21]=[CH:20][C:19]([C:22]([CH3:24])([CH3:23])[CH3:25])=[CH:18][CH:17]=1)=[O:10])[CH3:7]

Participants

4

Reactant 2

HCID 58873061HCID 58873061, compoundHCID 178418750HCID 178418750, compound

Product 1

HCID 58873184Ethyl 4-cyano-3-[4-(1,1-dimethylethyl)phenyl]-5-ethyl-2-thiophenecarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add diethylzinc (1.0M in hexanes, 16 mL, 16 mmol) to a solution of 3-(4-tert-butyl-phenyl)-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 over silica gel with 100% toluene to give the title compound as a clear oil, 625 mg (66%). MS (FAB)=341 (M+); HPLC=98%.

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-1545393b14fa456cbb2b76ebd8f82a5d
Source dataset
uspto-grants-2010_01
Patent number
US07642361B2

Reaction notes

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