Boron trifluoride → 1-Naphthol

HRID 843503

Reaktionsgleichung

Reaktionsgleichung von HRID 843503
C([O:4][C@@H:5]1[O:27][C@H:26]([CH2:28][O:29][C:30](=O)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C@@H:16]([O:17]C(=O)C2C=CC=CC=2)[C@H:6]1[O:7]C(=O)C1C=CC=CC=1)(=O)C.[C:38]1([OH:48])[C:47]2[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH:41]=[CH:40][CH:39]=1.B(F)(F)F>ClCCl>[O:29]([C:30]1[C:31]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:47]=[CH:38][CH:39]=1)[C@@H:28]1[O:7][C@H:6]([CH2:5][OH:4])[C@@H:16]([OH:17])[C@H:26]1[OH:27].[C:38]1([OH:48])[C:47]2[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH:41]=[CH:40][CH:39]=1

Komponenten

6

Edukt 3

HCID 6356Boron trifluorideHCID 70051-NaphtholHCID 81455beta-D-Ribofuranose, 1-acetate 2,3,5-tribenzoate

Produkt 2

HCID 70051-NaphtholHCID 18731516HCID 18731516, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (500 mg, 0.99 mmol), α-naphthol (428 mg, 3.00 mmol) and boron trifluoride diethyletherate (141 mg, 0.99 mmol. 125 μl) in dry dichloromethane (5 ml) was stirred at room temperature under argon for 16 hours. The mixture was worked up as for Stage 1 of Example 1 and purified by flash chromatography on silica gel (eluting with dichloromethane:hexanes, 3:2) to afford the title compound contaminated with α-naphthol. The latter was removed by dissolving the residue in ethyl acetate and washing with 10% aqueous sodium hydroxide solution, which after conventional processing, gave 136 mg, 23% of product as a yellow gum.

Aufarbeitung

  1. custompurified by flash chromatography on silica gel (eluting with dichloromethane:hexanes, 3:2)

Quellen und Nachweise

ORD-Eintrag
ord-d29c5ad3b72a470cbe102ea3c53a1c86
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06379911B2

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