Hydrochloric Acid → HCID 9888828, compound

HRID 619641Notes

Reaction equation

HRID 619641 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]#[C:19][C:20]4[CH:30]=[CH:29][C:23]([C:24]([O:26]CC)=[O:25])=[C:22]([F:31])[CH:21]=4)[CH:16]=3)[S:11][C:10]([CH3:33])([CH3:32])[CH:9]=2)=[CH:4][CH:3]=1.[OH-].[Na+].Cl>C1COCC1.CCO>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]#[C:19][C:20]4[CH:30]=[CH:29][C:23]([C:24]([OH:26])=[O:25])=[C:22]([F:31])[CH:21]=4)[CH:16]=3)[S:11][C:10]([CH3:33])([CH3:32])[CH:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21846662HCID 21846662, compound2×

Product 1

HCID 9888828HCID 9888828, compoundYield 83.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of ethyl 4-[[4-(4-methylphenyl)-2,2-dimethyl-(2H)-thiochromen-6-yl]-ethynyl]-2-fluorobenzoate (Compound 236, 100.0 mg, 0.219 mmol) in 3.0 mL THF and 3.0 mL EtOH was added NaOH (80.0 mg, 2.0 mmol, 2.0 mL of a 1M aqueous solution). The resulting solution was heated to 40° C. and stirred overnight. Upon cooling to 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 78.0 mg (83%) of the title compound as a pale-yellow solid. 1H NMR (300 MHz, d6 -acetone) δ: 7.94 (1H, d, J=7.8 Hz), 7.43-7.17 (9H, m), 5.93 (1H, s), 2.38 (3H, s), 1.47 (6H, s).

Workup

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

Sources & evidence

ORD record
ord-25f99d384e9542119f1110fc4a777bbf
Source dataset
uspto-grants-1999_09
Patent number
US05958954

Reaction notes

Loading…