HCID 86671497, compound → HCID 67255935, compound

HRID 536619Notes

Reaction equation

HRID 536619 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10](/[CH:14]=[CH:15]/[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:11][S:12][CH:13]=2)=[C:5]([CH3:21])[CH:4]=1)#[N:2]>CCO.[Pd]>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]([CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:11][S:12][CH:13]=2)=[C:5]([CH3:21])[CH:4]=1)#[N:2]

Participants

4

Reactant 1

HCID 86671497HCID 86671497, compound

Product 1

HCID 67255935HCID 67255935, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of (E)-ethyl 3-(4-(4-cyano-2-methylphenyl)thiophen-3-yl)acrylate (1 g, 3.4 mmol) in EtOH (20 mL) was added 10% Pd/C (w/w, 400 mg), and the mixture was stirred at room temperature under 1 atm of H2 overnight. The reaction mixture was filtered, and concentrated to give ethyl 3-(4-(4-cyano-2-methylphenyl)thiophen-3-yl)propanoate (Scheme III, 15, X1=4-cyano-2-methylphenyl) (0.9 g, yield 90%) as gray oil. 1H NMR (CD3OD 400 MHz): δ 7.69 (s, 1H), 7.60 (dd, J=8 Hz, J=1.2 Hz, 1H), 7.34 (d, J=8 Hz, 1H), 7.26-7.23 (m, 2H), 4.05 (q, J=7.2 Hz, 2H), 2.67 (t, J=7.6 Hz, 2H), 2.45 (t, J=7.6 Hz, 2H), 2.19 (s, 3H), 1.19 (t, J=7.2 Hz, 3H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-67f6e3a1f88746c3a1e55fef16ff4d48
Source dataset
uspto-grants-2014_10
Patent number
US08859611B2

Reaction notes

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