Water → HCID 9819936, compound

Participants

Reaction Conditions

Reaction Steps

To tetrahydrofuran (25 ml) is added a 3.4M solution of sodium bis(methoxyethoxy)aluminumhydride in toluene (18.0 ml), and the mixture is cooled to -10° C. To the mixture is added dropwise a suspension of 1-(4-pyridyl)-2,3-bis(methoxycarbonyl)-6,7-diethoxynaphthalene (10.0 g) in tetrahydrofuran (25 ml) over a period of time for 15 minutes. The reaction solution is warmed, and stirred under ice-cooling for 1.5 hour, and thereto is added 15% aqueous sodium hydroxide solution (3.7 ml). To the reaction mixture are added water and methylene chloride, and the insoluble materials are removed by filtration. The filtrate is extracted with methylene chloride, and the extract is washed, dried, and concentrated to give 1-(4-pyridyl)-2,3-bis(hydroxymethyl)-6,7-diethoxynaphthalene (7.89 g).

Provenance & Evidence