Ethyl Acetate → HCID 12564414, compound

To a suspension of ethyl-5-chloro-benzofuran carboxylate (1.05 g), prepared according to Helv. Chim. Acta., 818 (1935), in tetrahydrofuran (10 ml) was added lithium aluminum hydride (0.1 g). The mixture was stirred at room temperature for 1 hour. Ethyl acetate (50 ml) was slowly added to the reaction mixture, and the whole mixture was poured onto water (50 ml). The organic extract was separated, washed with water (2×25 ml), dried and evaporated to obtain 2-hydroxymethyl-5-cnlorobenzofuran as an oil [0.87 g; 'HNMR (CDCl3, 60 MHz): 4.6 (s, 2H), 6.6-7.4 (m, 4H)]. This material was added to a solution of methanesulfonyl chloride (1.15 g) in methylene chloride (20 ml) containing pyridine (1 ml). After stirring the reaction overnight it was poured onto ice-water (20 ml) and the organic extract was first washed with 10% HCl (5 ml) and then with water (2×10 ml). The washed extract was dried and evaporated to obtain 2-chloromethyl-5-chlorobenzofuran as a clear oil (yield: 0.5 g); HNMR (CDCl3, 60 MHz): 4.65 (s, 2H), 6.6 (s, 1H), 6.8-7.4 (m, 3H).

1. customprepared
2. additionthe whole mixture was poured onto water (50 ml)
3. extractionThe organic extract
4. customwas separated
5. washwashed with water (2×25 ml)
6. customdried
7. customevaporated
8. customto obtain 2-hydroxymethyl-5-cnlorobenzofuran as an oil [0.87 g
9. stirringAfter stirring
10. customthe reaction overnight it
11. additionwas poured onto ice-water (20 ml)
12. extractionthe organic extract
13. washwas first washed with 10% HCl (5 ml)
14. extractionThe washed extract
15. customwas dried
16. customevaporated

ORD record

ord-74ec5ea09a564d7285053e9812c612c1

Source dataset

uspto-grants-1990_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04939140