Hydrochloric Acid → HCID 9800008, compound

HRID 619658Notes

Reaction equation

HRID 619658 reaction equation
[C:1]1([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)[O:10][C:9]([CH3:31])([CH3:30])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].Cl>C1COCC1.CCO>[C:1]1([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)[O:10][C:9]([CH3:31])([CH3:30])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21846650HCID 21846650, compound2×

Product 1

HCID 9800008HCID 9800008, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
35 °C

Procedure

To a solution of ethyl 4-[[4-phenyl-2,2-dimethyl-(2H)-chromen-6-yl]-ethynyl]-benzoate (Compound 265, 70.0 mg, 0.171 mmol) in 3.0 mL THF and 3.0 mL EtOH was added NaOH (120.0 mg, 3.0 mmol, 3.0 mL of a 1M aqueous solution). The resulting solution was heated to 35° C., cooled to room temperature and stirred overnight. The reaction 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 the solvent was removed under reduced pressure. The residual solid was recrystallized from CH3CN to give 48.0 mg (74%) of the title compound as a colorless solid. 1H NMR (300 MHz, d6 -acetone) δ: 8.00 (2H, d, J=8.2 Hz), 7.57 (2H, d, J=8.2 Hz), 7.51-7.37 (6H, d), 7.14 (1H, d, J=2.0 Hz), 6.91 (1H, d, J=8.3 Hz), 5.80 (1H, s), 1.50 (6H, s),

Workup

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

Sources & evidence

ORD record
ord-35bd92579aa847e885a450d047194e63
Source dataset
uspto-grants-1999_09
Patent number
US05958954

Reaction notes

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