Tetrahydrofuran → HCID 86711814, compound

HRID 623724Notes

Reaction equation

HRID 623724 reaction equation
[CH2:1]([N:8]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)=[C:9]1[C:20]([O:22]CC)=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1COCC1.[OH-].[Na+]>CO>[CH2:1]([N:8]1[CH:12]=[CH:11][C:10]([C:13]2[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=2)=[C:9]1[C:20]([OH:22])=[O:21])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 86711815HCID 86711815, compound

Product 1

HCID 86711814HCID 86711814, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 1-benzyl-3-(4-chlorophenyl)-1H-pyrrole-2-carboxylate (8 g, 23.54 mmol) was dissolved in MeOH (33.4 mL) and THF (33.4 mL) followed by addition of aqueous 6M NaOH (33.4 mL, 200 mmol) and the reaction mixture was stirred at reflux for 18 h. The volatile solvents were evaporated under reduced pressure. The remaining aqueous phase was acidified with aqueous 1M HCl until pH=4 and a solid precipitated. The solid was filtered off and washed with cold H2O. The collected solid was dissolved in EtOAc, dried over Na2SO4, filtered and the solution evaporated to dryness to give 6.69 g (91%) of ACI-01.

Workup

  1. temperatureat reflux for 18 h
  2. customThe volatile solvents were evaporated under reduced pressure
  3. customa solid precipitated
  4. filtrationThe solid was filtered off
  5. washwashed with cold H2O
  6. dissolutionThe collected solid was dissolved in EtOAc
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customthe solution evaporated to dryness
  10. customto give 6.69 g (91%) of ACI-01

Sources & evidence

ORD record
ord-6740f34373db4f1894361e46dfee35a8
Source dataset
uspto-grants-2016_04
Patent number
US09302988B2

Reaction notes

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