Reaktion #952145

Reaktionsgleichung

2-chloropropionitrile

HCl

methyl 3-hydroxy-5-methoxybenzo[b]thiophene-2-carboxylate

potassium t-butoxide

→

3-(1-Cyanoethoxy)-5-methoxy-benzo[b]thiophene-2-carboxylic acid methyl ester

Lösungsmittel

ethyl acetate

DMSO

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthen warmed to 82° C. for 3 hours
2. 2
   WaschenThe organic layer is washed with 1N HCl
3. 3
   Trocknendried over MgSO4
4. 4
   FiltrationFiltration
5. 5
   Sonstigefollowed by removal of solvent in vacuo and recrystallization of the residue from ethyl acetate
6. 6
   Sonstigehexane gives 853 mg, mp 127°-129° C.

Vorschrift

To a room temperature solution of methyl 3-hydroxy-5-methoxybenzo[b]thiophene-2-carboxylate (1.00 g, 4.2 mmol) [Connor, et al., J. Med. Chem. 35:958 (1992)] in 20 mL of DMSO is added potassium t-butoxide (494 mg, 4.41 mmol) followed by 2-chloropropionitrile (1.1 mL, 12.6 mmol). The mixture is stirred at room temperature for 1.5 hours then warmed to 82° C. for 3 hours. The reaction mixture is poured into ethyl acetate and 1N HCl. The organic layer is washed with 1N HCl, followed by several portions of brine and dried over MgSO4. Filtration followed by removal of solvent in vacuo and recrystallization of the residue from ethyl acetate:hexane gives 853 mg, mp 127°-129° C.

Quelle