Hantzsch ester → 2-Cyano-3-{4-[2-(4-methanesulfonyloxyphenyl)ethoxy]phenyl}propanoic acid ethyl ester

HRID 987231Notes

Reaction equation

HRID 987231 reaction equation
[CH2:1]([O:3][C:4](=[O:29])[C:5]([C:27]#[N:28])=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][S:23]([CH3:26])(=[O:25])=[O:24])=[CH:18][CH:17]=2)=[CH:9][CH:8]=1)[CH3:2].C(OC(C1CC(C(OCC)=O)=C(C)NC=1C)=O)C>C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:29])[CH:5]([C:27]#[N:28])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][S:23]([CH3:26])(=[O:25])=[O:24])=[CH:18][CH:17]=2)=[CH:11][CH:12]=1)[CH3:2]

Participants

4

Reactant 2

HCID 70849Hantzsch esterHCID 865950572-Cyano-3-{4-[2-(4-methanesulfonyloxyphenyl)ethoxy]phenyl}acrylic acid ethyl ester

Product 1

HCID 179303192-Cyano-3-{4-[2-(4-methanesulfonyloxyphenyl)ethoxy]phenyl}propanoic acid ethyl esterYield 91.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-cyano-3-{4-[2-(4-methanesulfonyloxyphenyl)ethoxy]phenyl}acrylic acid ethyl ester (described in Example 6) (1.69 g; 4.07 mmole) and diethyl-1,4-dihydro-2,6-dimethyl-3,5-pyridine dicarboxylate (2.06 g; 8.14 mmole) was slowly heated to more than 190° C. under vacuum and thereafter allowed to cool to room temperature. The crude product was purified by chromatography on silica gel using heptane:ethyl acetate (gradient 2:1 to 1:1) as eluant to give 1.55 g (yield 91%) of 2-cyano-3-{4-[2-(4-methanesulfonyloxyphenyl)ethoxy]phenyl}propanoic acid ethyl ester.

Workup

  1. temperaturewas slowly heated to more than 190° C. under vacuum
  2. customThe crude product was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-7dbb3cbed128447c9ca3d37202a0eeb9
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

Loading…