Hydrochloric Acid → HCID 9910900, Verbindung

HRID 619662Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 619662
[CH3:1][C:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([C:21]#[C:22][C:23]4[CH:33]=[CH:32][C:26]([C:27]([O:29]CC)=[O:28])=[CH:25][CH:24]=4)[CH:19]=3)[O:14][C:13]([CH3:35])([CH3:34])[CH:12]=2)=[CH:7][CH:6]=1)([CH3:4])[CH3:3].[OH-].[Na+].Cl>C1COCC1.CCO>[CH3:4][C:2]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([C:21]#[C:22][C:23]4[CH:24]=[CH:25][C:26]([C:27]([OH:29])=[O:28])=[CH:32][CH:33]=4)[CH:19]=3)[O:14][C:13]([CH3:35])([CH3:34])[CH:12]=2)=[CH:9][CH:10]=1)([CH3:1])[CH3:3]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21846663HCID 21846663, Verbindung2×

Produkt 1

HCID 9910900HCID 9910900, VerbindungAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
35 °C

Versuchsvorschrift

To a solution of ethyl 4-[[4-(4-(1,1-dimethylethyl)phenyl)-2,2-dimethyl(2H)-chromen-6-yl]-ethynyl]-benzoate (Compound 269, 72.0 mg, 0.155 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 50.0 mg (74%) the title compound as a colorless solid. 1H NMR (300 MHz, d6 -acetone) δ: 8.00 (2H, d, J=8.3 Hz), 7.57 (2H, d, J=8.3 hz), 7.51 (2H, d, J=8.3 Hz), 7.41 (1H, dd, J=2.0, 8.3 Hz), 7.31 (2H, d, J=8.3 Hz), 7.19 (1H, d, J=2.0 Hz), 6.91 (1H, d, J=8.3 Hz), 5.78 (1H, s), 1.49 (6H, s), 1.35 (9H, s).

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-5c68ec1998da41db9d11a502c7300f62
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05958954

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