Hantzsch ester → 2-Cyano-3-{4-[2-(4-methylsulfonyloxyphenyl)ethoxy]phenyl}propanol

HRID 987127Notes

Reaction equation

HRID 987127 reaction equation
C([O:3][C:4](=O)[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)C.C(OC(C1CC(C(OCC)=O)=C(C)NC=1C)=O)C>C(OCC)(=O)C>[C:27]([CH:5]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH2:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]([O:22][S:23]([CH3:26])(=[O:25])=[O:24])=[CH:20][CH:21]=2)=[CH:11][CH:12]=1)[CH2:4][OH:3])#[N:28]

Participants

4

Reactant 2

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

Product 1

HCID 229884072-Cyano-3-{4-[2-(4-methylsulfonyloxyphenyl)ethoxy]phenyl}propanolYield 101.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 2-cyano-3-{4-[2 (4-methylsulfonyloxypbenyl)ethoxy]phenyl } propanoate A mixture of compound (a) (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 the desired product.

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-d198804091274d3eb5a860fb8049d1da
Source dataset
uspto-grants-2003_10
Patent number
US06630509B2

Reaction notes

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