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Hydrochloric Acid → 4-[[4-(5-methyl-thiophen-2-yl)-2,2-dimethyl-(2H)-thiochromen-6-yl]-ethyl]benzoic acid

HRID 619638
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 619638
[CH2:1]([C:3]1[S:7][C:6]([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:5][CH:4]=1)C.C(C1(C2C3C(=CC=C(C#CC4C=CC(C(OCC)=O)=CC=4)C=3)SC(C)(C)C=2)CC=CS1)C.[OH-].[Na+].Cl>C1COCC1.CCO>[CH3:1][C:3]1[S:7][C:6]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([CH2:18][CH2:19][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:5][CH:4]=1
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Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21846694ethyl 4-[[4-(5-ethylthiophen-2-yl)-2,2-dimethyl-(2H)-thiochromen-6-yl]-ethynyl]-benzoateHCID 86754562HCID 86754562, Verbindung

Produkt 1

HCID 218466784-[[4-(5-methyl-thiophen-2-yl)-2,2-dimethyl-(2H)-thiochromen-6-yl]-ethyl]benzoic acidAusbeute 73,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of ethyl 4-[[4-(5-ethylthiophen-2-yl)-2,2-dimethyl-(2H)-thiochromen-6-yl]-ethynyl]-benzoate (Compound 231, 23.0 mg, 0.05 mmol) in 1.0 mL THF and 1.0 mL EtOH was added NaOH (40.0 mg, 1.0 mmol, 1.0 mL of a 1M aqueous solution). The resulting solution was stirred overnight at 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 CH3CN to give 15.5 mg (72%) of the title compound as an orange solid. 1H NMR (300 MHz, d6 -acetone) δ: 8.03 (2H, d, J=8.3 Hz), 7.63 (2H, d, J=8.3 Hz), 7.61 (1H, s), 7.44 (2H, s), 6.90 (1H, d, J=3.5 Hz), 6.83 (1H, d, J=3.5 Hz), 6.10 (1H, s), 2.86 (2H, q, J=7.6 Hz), 1.45 (6H, s), 1.30 (3H, t, J=7.6 Hz).

Aufarbeitung

  1. extractionextracted with EtOAc
  2. washThe combined organic layers were washed with H2O, saturated aqueous NaCl
  3. dry with materialdried (Na2SO4)
  4. custombefore removing the solvent under reduced pressure
  5. customThe residual solid was recrystallized from CH3CN

Quellen und Nachweise

ORD-Eintrag
ord-c486651665d34fe09127ea2cf088f24d
Quelldatensatz
uspto-grants-1999_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05958954

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