Hydrochloric Acid → HCID 21846677, compound

HRID 619663Notes

Reaction equation

[F:1][C:2]1[CH:12]=[C:11]([C:13]#[C:14][C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[O:21][C:20]([CH3:26])([CH3:25])[CH:19]=[C:18]3[C:27]2[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=2)[CH:10]=[CH:9][C:3]=1[C:4]([O:6]CC)=[O:5].[OH-].[Na+].Cl>C1COCC1.CCO>[F:1][C:2]1[CH:12]=[C:11]([C:13]#[C:14][C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[O:21][C:20]([CH3:26])([CH3:25])[CH:19]=[C:18]3[C:27]2[CH:28]=[CH:29][C:30]([CH3:33])=[CH:31][CH:32]=2)[CH:10]=[CH:9][C:3]=1[C:4]([OH:6])=[O:5]

Participants

Conditions

Temperature: 35 °C

Procedure

To a solution of ethyl 2-fluoro-4-[[4-(4-methylphenyl)-2,2-dimethyl-(2H)-chromen-6-yl]-ethynyl]-benzoate (Compound 272, 60.0 mg, 0.136 mmol) in 2.0 mL THF and 1.0 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 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 the solvent was removed under reduced pressure. The residual solid was recrystallized from CH3CN to give 53.0 mg (94%) the title compound as a colorless solid. 1H NMR (300 MHz, d6 -acetone) δ: 7.93 (1H, d, J=7.8 Hz), 7.43-7.16 (8H, m), 6.91 (1H, d, J=8.3 Hz), 5.77 (1H, s), 2.38 (3H, s), 1.49 (6H, s).

Workup

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

Sources & evidence

ORD record: ord-14abf14cfb9245d789071ad5cce3293c
Source dataset: uspto-grants-1999_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05958954

Reaction notes

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