Diisobutylaluminum hydride → HCID 58044012, compound

Temperature

-78 °C

In a flask under N2, 186a (500 mg, 1.5 mmol) was suspended in methylene chloride and cooled to −78° C. in a dry ice/acetone bath. 1.0M DIBAL-H in methylene chloride (4.4 mL, 4.4 mmol) was slowly added via syringe. After the addition was complete the reaction was allowed to warm to −20° C. at which time the dry ice/acetone bath was exchanged for a ice/water bath and the reaction stirred an additional 0.5 hr at which time it was slowly quenched with 1N HCl (˜5 mL). The reaction was then diluted with ethyl acetate and allowed to stir and warm to room temp over ˜1 hr. The pH was adjusted to ˜7 with 1N NaOH and 50 mL of saturated aqueous Rochelle's salt was added and the mixture heated and stirred at 40° C. for 1 hr during which time the mixture cleared. The layers were separated, the organics washed with brine, dried over Na2SO4, filtered and concentrated to give 186b as a white solid (420 mg, 90% yield).

1. additionAfter the addition
2. customwas exchanged for a ice/water bath
3. customwas slowly quenched with 1N HCl (˜5 mL)
4. additionThe reaction was then diluted with ethyl acetate
5. stirringto stir
6. temperaturewarm to room temp over ˜1 hr
7. additionwas added
8. temperaturethe mixture heated
9. stirringstirred at 40° C. for 1 hr during which time the mixture
10. customThe layers were separated
11. washthe organics washed with brine
12. dry with materialdried over Na2SO4
13. filtrationfiltered
14. concentrationconcentrated

ORD record

ord-1c3458e7042d49e4b4f47086cc4e3d27

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08618107B2