Hydrochloric Acid → HCID 21846652, compound

HRID 619635Notes

Reaction equation

HRID 619635 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20]#[C:21][C:22]4[CH:32]=[CH:31][C:25]([C:26]([O:28]CC)=[O:27])=[CH:24][CH:23]=4)[CH:18]=3)[S:13][C:12]([CH3:34])([CH3:33])[CH:11]=2)=[CH:6][CH:5]=1)(C)[CH3:2].[OH-].[Na+].Cl>C1COCC1.CCO>[CH2:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([CH2:20][CH2:21][C:22]4[CH:23]=[CH:24][C:25]([C:26]([OH:28])=[O:27])=[CH:31][CH:32]=4)[CH:18]=3)[S:13][C:12]([CH3:33])([CH3:34])[CH:11]=2)=[CH:8][CH:9]=1)[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21846660ethyl 4-[[4-(4-isopropylphenyl)-2,2-dimethyl-(2H)-thiochromen-6-yl]-ethynyl]-benzoate2×

Product 1

HCID 21846652HCID 21846652, compoundYield 95.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of ethyl 4-[[4-(4-isopropylphenyl)-2,2-dimethyl-(2H)-thiochromen-6-yl]-ethynyl]-benzoate (Compound 228, 89.0 mg, 0.19 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 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 78.0 mg (93%) of the title compound as a pale-yellow solid. 1H NMR (300 MHz, d6 -acetone) δ: 8.00 (2H, d, J=8.4 Hz), 7.58 (2H, d, J=8.4 Hz), 7.45-7.21 (7H, m), 5.93 (1H, s), 2.95 (1H, hept, J=7.0 Hz), 1.47 (6H, s), 1.25 (6H, d, J=7.0 Hz).

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-4b48cb6e610a408e9e9c459776014580
Source dataset
uspto-grants-1999_09
Patent number
US05958954

Reaction notes

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