HCID 66724243, compound → HCID 66718108, compound

HRID 2194872Notes

Reaction equation

HRID 2194872 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1/[CH:9]=[CH:10]/[C:11]([O:13][CH2:14][CH3:15])=[O:12]>C1(C)C=CC=CC=1.CCOCC>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

4

Reactant 1

HCID 66724243HCID 66724243, compound

Product 1

HCID 66718108HCID 66718108, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of commercially available ethyl (2E)-3-(2-bromo-6-methylphenyl)acrylate (1 eq.) in toluene (0.1M) at reflux was added benzenesulfonyl hydrazide (3 eq). The reaction mixture was refluxed for 3 h, cooled to room temperature, and diluted with Et2O. The organic phase was washed with aqueous 1N NaOH, brine, dried over MgSO4 filtered and concentrated. Purification by column chromatography on silica gel (Combi-Flash by ISCO), eluting with Hex/EtOAc (0 to 20%, in 30 min) afforded the desired compound.

Workup

  1. temperatureThe reaction mixture was refluxed for 3 h
  2. washThe organic phase was washed with aqueous 1N NaOH, brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by column chromatography on silica gel (Combi-Flash by ISCO)
  7. washeluting with Hex/EtOAc (0 to 20%, in 30 min)

Sources & evidence

ORD record
ord-4191ec642013422ba943d6cc4e081e49
Source dataset
uspto-grants-2012_12
Patent number
US08334308B2

Reaction notes

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