Aluminium lithium hydride → HCID 58168467, compound

A solution of lithium aluminum hydride (2M in THF, 2.2 mL) was added portionwise over 5 minutes to a solution of 3-(3-ethoxy-3-oxopropylthio)benzoic acid [Aromatic Intermediate 15, step a] (1.0 g) in THF (20 mL), pre-cooled in ice-water. After ˜½ the addition the mixture formed a thick precipitate and was diluted with more THF (15 mL) to maintain stirring. The mixture was removed from the cooling bath and stirred at room temperature for 3.5 hours. The mixture was cooled back down in ice-water and treated with more lithium aluminum hydride (2M in THF, 2.2 mL). The mixture was removed from the cooling bath and stirred at room temperature overnight. The cloudy solution was cooled in ice water and then quenched by the careful addition of methanol (5 mL), added portionwise over 30 minutes. After ˜½ of the addition, the mixture was removed from the cooling bath and allowed to warm to room temperature for 45 minutes. The mixture was poured into aqueous HCl (2M) and extracted three times with ethyl acetate. The combined organic extracts were washed with brine, dried over anhydrous magnesium sulphate, filtered and concentrated under reduced pressure to give the subtitled compound as a pale yellow oil. Yield 0.55 g.

1. additionthe addition the mixture
2. customformed a thick precipitate
3. temperatureto maintain
4. customThe mixture was removed from the cooling bath
5. stirringstirred at room temperature for 3.5 hours
6. temperatureThe mixture was cooled back down in ice-water
7. additiontreated with more lithium aluminum hydride (2M in THF, 2.2 mL)
8. customThe mixture was removed from the cooling bath
9. stirringstirred at room temperature overnight
10. temperatureThe cloudy solution was cooled in ice water
11. customquenched by the careful addition of methanol (5 mL)
12. additionadded portionwise over 30 minutes
13. additionAfter ˜½ of the addition
14. customthe mixture was removed from the cooling bath
15. additionThe mixture was poured into aqueous HCl (2M)
16. extractionextracted three times with ethyl acetate
17. washThe combined organic extracts were washed with brine
18. dry with materialdried over anhydrous magnesium sulphate
19. filtrationfiltered
20. concentrationconcentrated under reduced pressure

ORD record

ord-cdf88049d6884f9bb09a6fcf801d73fa

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08455483B2