Hydrochloric Acid → HCID 11454785, Verbindung

HRID 1373867Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1373867
C([O:3][C:4](=[O:33])[CH2:5][O:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:17]3[S:21][C:20]4[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=4[C:18]=3[C:26](=[O:31])[CH2:27][CH2:28][CH2:29][CH3:30])[CH:13]=2)[C:8]=1[Br:32])C.[OH-].[K+].Cl>C1COCC1.O>[Br:32][C:8]1[C:9]2[C:14](=[CH:13][C:12]([C:17]3[S:21][C:20]4[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=4[C:18]=3[C:26](=[O:31])[CH2:27][CH2:28][CH2:29][CH3:30])=[CH:11][CH:10]=2)[CH:15]=[CH:16][C:7]=1[O:6][CH2:5][C:4]([OH:33])=[O:3]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 69411771[1-Bromo-6-(3-pentanoyl-benzo[b]thiophen-2-yl)-naphthalen-2-yloxy]-acetic acid ethyl ester

Produkt 1

HCID 11454785HCID 11454785, VerbindungAusbeute 75,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of [1-bromo-6-(3-pentanoyl-benzo[b]thiophen-2-yl)-naphthalen-2-yloxy]-acetic acid ethyl ester (0.0932 g, 0.177 mmol) and potassium hydroxide (0.063 gm 1.1 mmol) in THF (5 mL) and water (5 mL) was stirred at ambient temperature for two hours. It was then poured in excess water and acidified with 2N hydrochloric acid. This was then extracted with ethyl acetate and washed with water and brine. The organic phase was dried with anhydrous magnesium sulfate, filtered, solvent evaporated and dried in vacuo at 64° C. for 25 hours to yield [1-bromo-6-(3-pentanoyl-benzo[b]thiophen-2-yl)-naphthalen-2-yloxy]-acetic acid as a light yellow solid (0.0662 g, 75.2%): MP: 164–5° C.; mass spectrum (+EI, [M+H]+) m/z 497/499. 1H NMR (500 MHz, DMSO-d6): δ13.0–13.2 (br, 1H), 8.24 (d, 1H, J=8.70 Hz), 8.07–8.13 (m, 3H), 7.95–7.97 (m, 1H), 7.76 (dd, 1H, J=8.78 Hz and 1.91 Hz), 7.45–7.51 (m, 3H), 5.02 (s, 2H), 2.42 (t, 2H, J=7.22 Hz), 1.40–1.46 (m, 2H), 0.97–1.04 (m, 2H), 0.58 ppm (t, 3H, J=7.41 Hz). Elemental Analysis for C25H21BrO4S: Calcd: C, 60.37; H, 4.26; N, 0.00; Found: C, 60.23; H, 4.35; N, 0.00.

Aufarbeitung

  1. extractionThis was then extracted with ethyl acetate
  2. washwashed with water and brine
  3. dry with materialThe organic phase was dried with anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customsolvent evaporated
  6. customdried in vacuo at 64° C. for 25 hours

Quellen und Nachweise

ORD-Eintrag
ord-e6878d6335194100b007a5b207769fe9
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07163954B2

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