Hydrochloric Acid → HCID 9866920、化合物

HRID 619661ノート

反応式

HRID 619661 の反応式
[CH3:1][CH:2]([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)[O:13][C:12]([CH3:34])([CH3:33])[CH:11]=2)=[CH:6][CH:5]=1)[CH3:3].[OH-].[Na+].Cl>C1COCC1.CCO>[CH3:3][CH:2]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20]#[C:21][C:22]4[CH:23]=[CH:24][C:25]([C:26]([OH:28])=[O:27])=[CH:31][CH:32]=4)[CH:18]=3)[O:13][C:12]([CH3:34])([CH3:33])[CH:11]=2)=[CH:8][CH:9]=1)[CH3:1]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21846687HCID 21846687、化合物2 回

生成物 1

HCID 9866920HCID 9866920、化合物収率 84.5%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
35 °C

実験手順

To a solution of ethyl 4-[[4-(4-(1-methylethyl)phenyl)-2,2-dimethyl-(2H)-chromen-6-yl]-ethynyl]-benzoate (Compound 268, 95.0 mg, 0.210 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 75.0 mg (84%) the title compound as a colorless solid. 1H NMR (300 MHz, CDCl3) δ: 8.05 (2H, d, J=8.4 Hz), 7.55 (2H, d, J=8.4 Hz), 7.36 (1H, dd, J=2.0, 8.3 Hz), 7.30-7.26 (5H, m), 6.88 (1H, d, J=8.3 Hz), 5.64 (1H, s), 2.98 (1H, hept, J=6.9 Hz), 1.51 (6H, s), 1.31 (6H, d, J=6.9 Hz).

後処理

  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

出典と根拠

ORDレコード
ord-5162a0785cc348cc95c6c8c60559ec07
出典データセット
uspto-grants-1999_09
特許番号
US05958954

反応ノート

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