Hydrochloric Acid → HCID 11419622, Verbindung

HRID 1373881Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1373881
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[Cl:32])C.[OH-].[K+].Cl>C1COCC1.O>[Cl: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 69412293HCID 69412293, Verbindung

Produkt 1

HCID 11419622HCID 11419622, VerbindungAusbeute 69,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of [1-chloro-6-(3-pentanoyl-benzo[b]thiophen-2-yl)-naphthalen-2-yloxy]-acetic acid ethyl ester (0.0701 g, 0.146 mmol) and potassium hydroxide (0.032 g, 0.57 mmoles) in THF (4 mL) and water (4 mL) was stirred for 1.5 hours at ambient temperature. 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 dried in vacuo at 60° C. for 14 hours to yield [1-chloro-6-(3-pentanoyl-benzo[b]thiophen-2-yl)-naphthalen-2-yloxy]-acetic acid as a yellow semi-solid (0.0462 g, 69.9%); Mass spectrum (+ES, [M+H]+) m/z 453; 1H NMR (500 MHz, DMSO-d6): δ12.9–13.5 (br, 1H), 8.26 (d, 1H, J=8.85 Hz), 8.16 (d, 1H, J=1.83 Hz), 8.09–8.10 (m, 2H), 7.97–7.99 (m, 1H), 7.77 (dd, 1H, J=8.70 and 1.83 Hz), 7.47–7.56 (m, 3H), 5.03 (s, 2H), 2.43 (t, 2H, J=7.25 Hz), 1.42–1.48 (m, 2H), 0.98–1.06 (m, 2H), 0.59 ppm (t, 3H, J=7.40 Hz). Elemental Analysis for C25H21ClO4S+0.2 moles H2O: Calcd: C, 65.77; H, 4.72; N, 0.00; Found: C, 65.74; H, 4.99; 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 60° C. for 14 hours

Quellen und Nachweise

ORD-Eintrag
ord-7cb381955d424d8490dd16f348e98685
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07163954B2

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