Hydrochloric Acid → HCID 9803296, compound

HRID 619645Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([O:31][CH3:32])=[C:15]([C:18]#[C:19][C:20]4[CH:30]=[CH:29][C:23]([C:24]([O:26]CC)=[O:25])=[CH:22][CH:21]=4)[CH:16]=3)[S:11][C:10]([CH3:34])([CH3:33])[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][C:14]([O:31][CH3:32])=[C:15]([C:18]#[C:19][C:20]4[CH:21]=[CH:22][C:23]([C:24]([OH:26])=[O:25])=[CH:29][CH:30]=4)[CH:16]=3)[S:11][C:10]([CH3:34])([CH3:33])[CH:9]=2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 45 °C

Procedure

To a solution of ethyl 4-[[4-(4-methylphenyl)-2,2-dimethyl-7-methoxy-(2H)-thiochromen-6-yl]-ethynyl]-benzoate (Compound 215, 64.0 mg, 0.113 mmol) in 2.0 mL THF and 2.0 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 45° 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 50 mg (83%) of the title compound as a colorless solid. 1H NMR (300 MHz, d6 -acetone) δ: 8.00 (2H, d, J=8.2 Hz), 7.56 (2H, d, J=8.2 Hz), 7.28-7.14 (5H, m), 7.06 (1H, s), 5.76 (1H, s), 3.96 (3H, s), 2.36 (3H, s), 1.47 (6H, s).

Workup

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

Sources & evidence

ORD record: ord-bb7c9615da6946efa83b667e596ab397
Source dataset: uspto-grants-1999_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05958954

Reaction notes

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