Hydrochloric Acid → 4-[[4-(5-methyl-thiophen-2-yl)-2,2-dimethyl-(2H)-thiochromen-6-yl]-ethynyl]-benzoic acid

HRID 619637Notes

Reaction equation

HRID 619637 reaction equation
[CH3:1][C:2]1[S:6][C:5]([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]#[C:18][C:19]4[CH:29]=[CH:28][C:22]([C:23]([O:25]CC)=[O:24])=[CH:21][CH:20]=4)[CH:15]=3)[S:10][C:9]([CH3:31])([CH3:30])[CH:8]=2)=[CH:4][CH:3]=1.[OH-].[Na+].Cl>C1COCC1.CCO>[CH3:1][C:2]1[S:6][C:5]([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]#[C:18][C:19]4[CH:20]=[CH:21][C:22]([C:23]([OH:25])=[O:24])=[CH:28][CH:29]=4)[CH:15]=3)[S:10][C:9]([CH3:31])([CH3:30])[CH:8]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21846701HCID 21846701, compound2×

Product 1

HCID 99537284-[[4-(5-methyl-thiophen-2-yl)-2,2-dimethyl-(2H)-thiochromen-6-yl]-ethynyl]-benzoic acidYield 82%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 4-[[4-(5-methylthiophen-2-yl)-2,2-dimethyl-(2H)-thiochromen-6-yl]-ethynyl]-benzoate (Compound 230, 143.0 mg, 0.322 mmol) in 3.0 mL THF and 3.0 mL EtOH was added NaOH (160.0 mg, 4.0 mmol, 4.0 mL of a 1M aqueous solution). The resulting solution was stirred overnight at room temperature. The reaction mixture was acidified with 10% aqueous HCl and extracted with EtOAc. The combined organic layers were washed with H2O, saturated aqueous NaCl, and dried (Na2SO4) before removing the solvent under reduced pressure. The residual solid was recrystallized from CH3CN to give 110.0 mg (82%) of the title compound as a pale-yellow solid. 1H NMR (300 MHz, d6 -acetone) δ: 8.03 (2H, d, J=8.4 Hz), 7.63 (2H, d, J=8.3 Hz), 7.60 (1H, s), 7.44 (2H, s), 6.87 (1H, d, J=3.5 Hz), 6.79 (1H, m), 6.10 (1H, s), 2.49 (3H, s), 1.45 (6H, s).

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic layers were washed with H2O, saturated aqueous NaCl
  3. dry with materialdried (Na2SO4)
  4. custombefore removing the solvent under reduced pressure
  5. customThe residual solid was recrystallized from CH3CN

Sources & evidence

ORD record
ord-d2cbd423c31c49319ac9edb18d81921c
Source dataset
uspto-grants-1999_09
Patent number
US05958954

Reaction notes

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