Hydrochloric Acid → HCID 15858319, compound

A solution of (±)-(trans)- 2-(2,3-dihydrobenzofuran-4-yl)-cyclopropanecarboxaldehyde (2.6 g, 15 mmol), hydroxylamine hydrochloride (3.13 g, 45 mmol), ethanol (60 mL), water (40 mL), and 10N NaOH (4.5 mL, 45 mmol) was heated to reflux for 4 h. The solution was cooled to room temperature, diluted with water and ethyl acetate. The ethyl acetate layer was separated and washed sequentially with H2O and brine. The ethyl acetate extract was dried over K2CO3 and concentrated in vacuo. The residue was dissolved in THF (50 mL) and added dropwise to a -45° C. suspension of LAH (1.06 g, 28 mmol) in THF (100 mL), maintaining the temperature below -40° C. The reaction was warmed to room temperature and stirred for 2 h. The reaction was recooled to -45° C., and 1N HCl (50 mL) was cautiously added dropwise. The cooling bath was removed and the suspension was stirred at room temperature for 30 min. The resulting paste was then diluted with ethyl ether and extracted with 1N HCl. The acid extracts were combined, washed with ethyl ether, made basic with 50% NaOH, and extracted with dichloromethane. The dichloromethane extracts were combined, washed with brine, dried over K2CO3, and concentrated in vacuo to give a clear oil (900 mg, 40%).

1. temperatureto reflux for 4 h
2. customThe ethyl acetate layer was separated
3. washwashed sequentially with H2O and brine
4. extractionThe ethyl acetate extract
5. dry with materialwas dried over K2CO3
6. concentrationconcentrated in vacuo
7. dissolutionThe residue was dissolved in THF (50 mL)
8. additionadded dropwise to a -45° C.
9. temperaturemaintaining the temperature below -40° C
10. temperatureThe reaction was warmed to room temperature
11. customwas recooled to -45° C.
12. customThe cooling bath was removed
13. stirringthe suspension was stirred at room temperature for 30 min
14. additionThe resulting paste was then diluted with ethyl ether
15. extractionextracted with 1N HCl
16. washwashed with ethyl ether
17. extractionextracted with dichloromethane
18. washwashed with brine
19. dry with materialdried over K2CO3
20. concentrationconcentrated in vacuo

ORD record

ord-b9e6a85c3e58409188e27470dc87aee2

Source dataset

uspto-grants-1999_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05856529