2-(4-Hydroxyphenyl)-5-benzofurancarboxylic acid → HCID 10192749, Verbindung

HRID 1794555Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1794555
[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>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

3

Edukt 1

HCID 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 1.0 M) and the reaction was heated to reflux. After 2 hr, the reaction was cooled and then poured into 2NHCl 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° C.; 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. additionpoured into 2NHCl and
  4. extractionextracted with EtOAc
  5. customThe organic layer was dried
  6. concentrationconcentrated
  7. customthe product was purified by cloumn chromatography (60% EtOAc/Hexane)

Quellen und Nachweise

ORD-Eintrag
ord-fdf7a05dbb194648b2c70f192899c877
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07022733B2

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