Lithium hydroxide, monohydrate → HCID 67480351, compound

HRID 623728Notes

Reaction equation

HRID 623728 reaction equation
[CH2:1]([N:8]1[CH:12]=[C:11]([CH3:13])[C:10]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[C:9]1[C:21]([O:23]CC)=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[Li].O>C1COCC1.CCO.O>[CH2:1]([N:8]1[CH:12]=[C:11]([CH3:13])[C:10]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[C:9]1[C:21]([OH:23])=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86711816HCID 86711816, compound

Product 1

HCID 67480351HCID 67480351, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of ethyl 1-benzyl-3-(4-chlorophenyl)-4-methyl-1H-pyrrole-2-carboxylate (8.50 g, 24.0 mmol) in THF (15 mL), EtOH (15 mL) and H2O (15 mL) was added LiOH.H2O (10.1 g, 240 mmol). The reaction mixture was stirred at reflux temperature for 2 h. To the reaction mixture were added extra H2O (45 mL) and EtOH (30 mL) and the reaction mixture was stirred at reflux temperature overnight. The reaction mixture was allowed to cool to room temperature and was almost completely concentrated. Aqueous 1 M KHSO4 (˜240 mL) was added to the reaction mixture while cooling with an ice-bath (pH reached 1), followed by the addition of EtOAc (500 mL). The organic layer was separated, washed with brine (2×400 mL), dried (Na2SO4) and concentrated. The residue was washed with a minimal amount of i-Pr2O and dried on a filter for 1 h to give ACI-02 (7.26 g, 93%).

Workup

  1. temperatureat reflux temperature for 2 h
  2. stirringthe reaction mixture was stirred
  3. temperatureat reflux temperature overnight
  4. concentrationwas almost completely concentrated
  5. additionAqueous 1 M KHSO4 (˜240 mL) was added to the reaction mixture
  6. temperaturewhile cooling with an ice-bath (
  7. additionfollowed by the addition of EtOAc (500 mL)
  8. customThe organic layer was separated
  9. washwashed with brine (2×400 mL)
  10. dry with materialdried (Na2SO4)
  11. concentrationconcentrated
  12. washThe residue was washed with a minimal amount of i-Pr2O
  13. customdried on
  14. filtrationa filter for 1 h
  15. customto give ACI-02 (7.26 g, 93%)

Sources & evidence

ORD record
ord-89f02150bedc4769a2b244e51054aab2
Source dataset
uspto-grants-2016_04
Patent number
US09302988B2

Reaction notes

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