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Phosphoric Acid → 2-(6-((5-(4-Chlorophenyl)isoxazol-3-yl)methoxy)-5-methylbenzo[b]thiophen-3-yl)acetic acid

HRID 1814183
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1814183
C[O:2][C:3](=[O:29])[CH2:4][C:5]1[C:6]2[CH:13]=[C:12]([CH3:14])[C:11]([O:15][CH2:16][C:17]3[CH:21]=[C:20]([C:22]4[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=4)[O:19][N:18]=3)=[CH:10][C:7]=2[S:8][CH:9]=1.[OH-].[K+].OP(O)(O)=O>O1CCCC1>[CH3:14][C:12]1[C:11]([O:15][CH2:16][C:17]2[CH:21]=[C:20]([C:22]3[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][CH:27]=3)[O:19][N:18]=2)=[CH:10][C:7]2[S:8][CH:9]=[C:5]([CH2:4][C:3]([OH:29])=[O:2])[C:6]=2[CH:13]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 1004Phosphoric AcidHCID 14797Potassium HydroxideHCID 69515759{5-Methyl-6-[5-(4-chloro-phenyl)-isoxazol-3-ylmethoxy]-benzo[b]thiophen-3-yl}-acetic acid methyl ester

Produkt 1

HCID 225048432-(6-((5-(4-Chlorophenyl)isoxazol-3-yl)methoxy)-5-methylbenzo[b]thiophen-3-yl)acetic acidAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

Compound 79A (0.03 g, 0.07 mmol) from the preceding step was dissolved in 2-3 mL of tetrahydrofuran, an equal volume of 2N KOH was added, and the mixture stirred at room temp. After 18 hours 75 mL of icewater was added and the mixture was acidified with H3PO4. After 30 min the precipitate was filtered off, rinsed 3× with water, and dried. The product was triturated in 4N HCl, allowed to stand for an hour, then filtered off, rinsed with water then ethanol, and dried to afford 0.01 g (99%) of the title compound as a white powder; mp 198-200° C. (dec). MS m/z 413 (M). Synthesis of {6-[5-(4-Trifluoromethyl-phenyl)-isoxazol-3-ylmethoxy]-benzofuran-3-yl}-acetic acid (Compound 80) Step 1. Preparation of {6-[5-(4-Trifluoromethyl-phenyl)-isoxazol-3-ylmethoxy]-benzofuran-3-yl}-acetic acid methyl ester (Compound 80A)

Aufarbeitung

  1. additionAfter 18 hours 75 mL of icewater was added
  2. filtrationAfter 30 min the precipitate was filtered off
  3. washrinsed 3× with water
  4. customdried
  5. customThe product was triturated in 4N HCl
  6. waitto stand for an hour
  7. filtrationfiltered off
  8. washrinsed with water
  9. dry with materialethanol, and dried

Quellen und Nachweise

ORD-Eintrag
ord-392ac451dd9440889e2e9b491eacc56f
Quelldatensatz
uspto-grants-2005_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06875780B2

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