Reaktion #51899

Reaktionsgleichung

sodium borohydride

ethyl 2-formyl-3-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxylate

CH2Cl2

→

title compound

Ausbeute 59.5%

Ethyl 7-hydroxy-2-(hydroxymethyl)-3-methylthieno[3,2-b]pyridine-6-carboxylate

Ausbeute 59.5%

Lösungsmittel

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigequenched by the addition of water (30 mL)
2. 2
   Temperaturto chill in an ice bath
3. 3
   workup.ADDITIONthe mixture was adjusted to pH 4 by the careful addition of 1 N HCl
4. 4
   workup.STIRRINGThe resulting thick mixture was stirred at 0° C. for one hour
5. 5
   Filtrationbefore filtering
6. 6
   WaschenThe collected solid was washed with water
7. 7
   Sonstigedried in vacuo

Vorschrift

A suspension of ethyl 2-formyl-3-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxylate (Preparation 3)(1.50 g, 5.66 mmol) in 1:1 CH2Cl2:MeOH (15 mL) was chilled in an ice bath before the addition of sodium borohydride (0.214 g, 5.66 mmol). The reaction was stirred at 0° C. for one hour and then quenched by the addition of water (30 mL). While continuing to chill in an ice bath, the mixture was adjusted to pH 4 by the careful addition of 1 N HCl. The resulting thick mixture was stirred at 0° C. for one hour before filtering. The collected solid was washed with water and dried in vacuo, affording the title compound (0.90 g) as an off-white solid. The filtrate was concentrated in vacuo to a volume of about 50 mL, more water was added, and the mixture was again filtered after chilling in ice, giving an additional 0.29 g of the title product.

Quelle