Hydrochloric Acid → HCID 12256609, compound

At room temperature, a solution of 10b (12.7 g; 5.0 mmol) in diethyl ether (75 ml) was added dropwise over a period of 2.5 h to a suspension of LiAlH4 (2.9 g; 7.6 mmol) in diethyl ether (50 ml). After the addition had ended, the reaction mixture was stirred at room temperature and with occasional addition of LiAlH4 until no more starting material could be detected by thin-layer chromatography (2.5 h). With ice-cooling, ice was introduced into the reaction mixture, and the aqueous phase was acidified with 10% hydrochloric acid (pH 1). The organic phase was removed and the aqueous phase was extracted with diethyl ether (3×). The combined organic extract was washed with 10% strength aqueous sodium hydroxide solution (4×50 ml) until it was virtually colorless. Dimethyl sulfate (9.0 g; 7.0 mmol) was added to the combined sodium hydroxide extract, and the mixture was stirred at room temperature for 16.5 h. The oily sediment was taken up in diethyl ether. The organic phase was separated off and the aqueous phase was again extracted with diethyl ether (2×). The combined organic extract was dried over Na2SO4 and concentrated. The brown oily residue was subjected to a kugelrohr distillation (0.2 mbar, 250° C.).

1. additionAfter the addition
2. customcould be detected by thin-layer chromatography (2.5 h)
3. temperatureWith ice-cooling
4. additionice was introduced into the reaction mixture
5. customThe organic phase was removed
6. extractionthe aqueous phase was extracted with diethyl ether (3×)
7. extractionThe combined organic extract
8. washwas washed with 10% strength aqueous sodium hydroxide solution (4×50 ml) until it
9. extractionextract
10. customThe organic phase was separated off
11. extractionthe aqueous phase was again extracted with diethyl ether (2×)
12. extractionThe combined organic extract
13. dry with materialwas dried over Na2SO4
14. concentrationconcentrated
15. distillationThe brown oily residue was subjected to a kugelrohr distillation (0.2 mbar, 250° C.)

ORD record

ord-7f89c731b69b43eb9f8a644e38ac892f

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07582660B2