Hydrochloric Acid → HCID 10192749, Verbindung

HRID 1836060Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1836060
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][C:14]([C:17](O)=[O:18])=[CH:13][C:11]=3[CH:12]=2)=[CH:4][CH:3]=1.Cl>C1COCC1>[OH:18][CH2:17][C:14]1[CH:15]=[CH:16][C:10]2[O:9][C:8]([C:5]3[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=3)=[CH:12][C:11]=2[CH:13]=1

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 222216192-(4-Hydroxyphenyl)-5-benzofurancarboxylic acid

Produkt 1

HCID 10192749HCID 10192749, VerbindungAusbeute 37 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Compound 143 (0.21 g, 0.83 mmol) in THF (10 ml) was treated with BH3 THF (4.0 ml of 1.0M) and the reaction was heated to reflux. After 2 hr, the reaction was cooled and then poured into 2N HCl and extracted with EtOAc. The organic layer was dried, concentrated and the product was purified by cloumn chromatography (60% EtOAc/Hexane) to give 144 as a solid (0.07 g, 37%); Mp=248-250°; 1H NMR (DMSO-d6) δ 9.86 (br s, 1 H), 7.72 (d, 2 H, J=8.3 Hz), 7.52-7.49 (m, 2 H), 7.19 (dd, 1 H, J=8.3 Hz, 1.6 Hz), 7.15 (s, 1 H), 6.87 (d, 2 H, J=8.8 Hz), 5.19 (t, 1 H, J=5.2 Hz), 4.56 (d, 2 H, J=4.1 Hz); MS 239 (M−H)−

Aufarbeitung

  1. temperaturethe reaction was heated to reflux
  2. temperaturethe reaction was cooled
  3. extractionextracted with EtOAc
  4. customThe organic layer was dried
  5. concentrationconcentrated
  6. customthe product was purified by cloumn chromatography (60% EtOAc/Hexane)

Quellen und Nachweise

ORD-Eintrag
ord-bf9ac396461c45feb5091c6a65ac59f7
Quelldatensatz
uspto-grants-2004_08
Patentnummer
US06774248B2

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