HCID 86671494, compound → HCID 67254892, compound

HRID 536611Notes

Reaction equation

HRID 536611 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:20]3[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=3)=[C:10](/[CH:13]=[CH:14]/[C:15]([O:17][CH2:18][CH3:19])=[O:16])[S:11][CH:12]=2)=[C:4]([O:27][CH3:28])[CH:3]=1>CCO.[Pd]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:20]3[CH:21]=[CH:22][C:23]([OH:26])=[CH:24][CH:25]=3)=[C:10]([CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[S:11][CH:12]=2)=[C:4]([O:27][CH3:28])[CH:3]=1

Participants

4

Reactant 1

HCID 86671494HCID 86671494, compound

Product 1

HCID 67254892HCID 67254892, compoundYield 86.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of (E)-ethyl 3-(4-(4-chloro-2-methoxyphenyl)-3-(4-hydroxyphenyl)thiophen-2-yl)acrylate (280 mg, 0.61 mmol) in EtOH (5 mL) was added Pd/C (50 mg). After the mixture was stirred at room temperature under H2 atmosphere for 4 hours, the mixture was filtered and concentrated in vacuo to give ethyl 3-(4-(4-chloro-2-methoxyphenyl)-3-(4-hydroxyphenyl)thiophen-2-yl)propanoate (Scheme II, 11, X1=4-hydroxyphenyl, X2=4-chloro-2-methoxyphenyl) (220 mg, yield 78%). 1H NMR (DMSO-d6 400 MHz): δ 9.34 (s, 1H), 7.26 (s, 1H), 7.01 (d, J=8.4 Hz, 1H), 6.90 (d, J=8.8 Hz, 2H), 6.79 (d, J=8.0 Hz, 2H), 6.64 (d, J=8.4 Hz, 2H), 4.04 (q, J=7.2 Hz, 2H), 3.40 (s, 3H), 2.96 (t, J=7.6 Hz, 2H), 2.55 (t, J=7.6 Hz, 2H), 1.16 (t, J=7.2 Hz, 3H).

Workup

  1. filtrationthe mixture was filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-25f15a69a57d479ea459e97fe6a6a1db
Source dataset
uspto-grants-2014_10
Patent number
US08859611B2

Reaction notes

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