Hydrochloric Acid → HCID 9821994, 화합물

HRID 619659노트

반응식

HRID 619659 반응식
[CH3:1][C:2]1[CH: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)[O: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[CH:3]=[CH:4][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)[O:11][C:10]([CH3:32])([CH3:31])[CH:9]=2)=[CH:6][CH:7]=1

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21846645HCID 21846645, 화합물2회

생성물 1

HCID 9821994HCID 9821994, 화합물수율 83.3%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
35 °C

실험 절차

To a solution of ethyl 4-[[4-(4-methylphenyl)-2,2-dimethyl-(2H)chromen-6-yl]-ethynyl]-benzoate (Compound 266, 90.0 mg, 0.213 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 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 70.0 mg (83%) the title compound as a colorless solid. 1H NMR (300 MHz, d6 -acetone) δ: 8.01 (2H, d, J=8.3 Hz), 7.57 (2H, d, J=8.3 Hz), 7.40 (1H, dd, J=2.1, 8.3 Hz), 7.30-7.20 (4H, m), 7.16 (1H, d, J=2.0 Hz), 6.90 (1H, d, J=8.3 Hz), 5.67 (1H, s), 2.38 (3H, s), 1.49 (6H, s).

후처리

  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

출처 및 근거

ORD 기록
ord-3c084b6c228a476a94fcf4ad777fedf5
출처 데이터셋
uspto-grants-1999_09
특허 번호
US05958954

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