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Hydrochloric Acid → 4-[[4-(6-methylpyridin-3-yl)-2,2-dimethyl-(2H)-thiochromen-6-yl]-ethynyl]-benzoic acid

HRID 619640
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HRID 619640 반응식
[CH3:1][C:2]1[N: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])=[CH:22][CH:21]=4)[CH:16]=3)[S:11][C:10]([CH3:32])([CH3:31])[CH:9]=2)=[CH:4][CH:3]=1.[OH-].[Na+].Cl>C1COCC1.CCO>[CH3:1][C:2]1[N: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:21]=[CH:22][C:23]([C:24]([OH:26])=[O:25])=[CH:29][CH:30]=4)[CH:16]=3)[S:11][C:10]([CH3:32])([CH3:31])[CH:9]=2)=[CH:4][CH:3]=1
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6

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HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21846679ethyl 4-[[4-(6-methylpyridin-3-yl)-2,2-dimethyl-(2H)-thiochromen-6-yl]-ethynyl]-benzoate2회

생성물 1

HCID 98229074-[[4-(6-methylpyridin-3-yl)-2,2-dimethyl-(2H)-thiochromen-6-yl]-ethynyl]-benzoic acid수율 92%

시약·촉매·용매 2

HCID 702Ethanol
용매
HCID 8028Tetrahydrofuran용매

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온도
35 °C

실험 절차

To a solution of ethyl 4-[[4-(6-methylpyridin-3-yl)-2,2-dimethyl-(2H)-thiochromen-6-yl]-ethynyl]-benzoate (Compound 233, 70.0 mg, 0.159 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 stirred overnight at 35° C. 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 acetone to give 60.0 mg (92%) of the title compound as a colorless solid. 1H NMR (300 MHz, d6 -acetone) δ: 8.36 (1H, d, J=2.1 Hz), 7.91 (2H, d, J=8.3 Hz), 7.60 (2H, d, J=8.3 Hz), 7.56 (1H, dd, J=2.1 8.0 Hz), 7.45 (2H, m), 7.31 (1H, d, J=8.0 Hz), 7.06 (1H, s), 6.06 (1H, s), 2.51 (3H, s), 1.44 (6H, s).

후처리

  1. temperatureUpon cooling to room temperature
  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 acetone

출처 및 근거

ORD 기록
ord-e5f0526873e740d2950b44ea2ffb1b38
출처 데이터셋
uspto-grants-1999_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05958954

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