Boron trifluoride → 1-Naphthol

HRID 843503

Reaction equation

HRID 843503 reaction equation
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

Participants

6

Reactant 3

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

Product 2

HCID 70051-NaphtholHCID 18731516HCID 18731516, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-d29c5ad3b72a470cbe102ea3c53a1c86
Source dataset
uspto-grants-2002_04
Patent number
US06379911B2

Linked notes

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