Hydrochloric Acid → HCID 9866920, Verbindung

HRID 619661Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 619661
[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]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21846687HCID 21846687, Verbindung2×

Produkt 1

HCID 9866920HCID 9866920, VerbindungAusbeute 84,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
35 °C

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-5162a0785cc348cc95c6c8c60559ec07
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05958954

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