Potassium Carbonate → HCID 69223009, compound

HRID 1027877Notes

Reaction equation

HRID 1027877 reaction equation
[C:1]([O:10][CH3:11])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[SH:4].Br[CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:11][O:10][C:1](=[O:9])[C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[S:4][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 76300Ethyl 4-bromobutyrate

Product 1

HCID 69223009HCID 69223009, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of methyl thiosalicylate (3.25 g, 19.3 mmol), ethyl 4-bromobutyrate (5.7 g, 29 mmol) and potassium carbonate (5.4 g, 39 mmol) in acetone (40 mL) was heated at reflux for 1 hour, cooled and filtered to remove the solids. The solids were washed with acetone and the combined filtrates were concentrated under reduced pressure and chromatographed on silica gel eluting with a gradient of hexane:EtOAc (20:1, 10:1, 5:1 and 2:1) to provide the title compound. 1H NMR (CDCl3) δ 1.26 (t, J=7.12 Hz, 3H), 2.05 (m, 2H), 2.51 (t, J=7.29 Hz, 2H), 2.99 (t, J=7.29 Hz, 2H), 3.91 (s, 3H), 4.14 (q, J=7.12 Hz, 2H), 7.11-7.21 (m, 1H), 7.35 (m, 1H), 7.45 (m, 1H), 7.95 (dd, J=7.80, 1.70 Hz, 1H); MS (M+NH4)+ m/z 300.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 hour
  3. temperaturecooled
  4. filtrationfiltered
  5. customto remove the solids
  6. washThe solids were washed with acetone
  7. concentrationthe combined filtrates were concentrated under reduced pressure
  8. customchromatographed on silica gel eluting with a gradient of hexane:EtOAc (20:1, 10:1, 5:1 and 2:1)

Sources & evidence

ORD record
ord-1e9e594678eb47dfad5fcf55fde768be
Source dataset
uspto-grants-2014_05
Patent number
US08735411B2

Reaction notes

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