Methanol → HCID 58128481, compound

Temperature

0 °C

1 M DiBAl—H in dichloromethane (42 mL, 2.2 eq.) was added slowly, via an addition funnel, over 20 min to a well stirred solution of the α,β-unsaturated ester from step 1 of this example (5.14 gram, 1 eq.) in anhydrous DCM (100 mL) under argon atmosphere at −78° C. The resulting solution was warmed to 0° C. after completion of addition and was kept at that temperature for 30 min. The reaction was cooled back to −78° C. and 4 mL MeOH was added slowly to quench the excess DiBAl-H. The cold solution was further stirred at −78° C. for 10 min before pouring into 150 mL saturated aqueous Rochelle (sodium potassium tartrate) salts solution. The mixture was vigorously stirred at room temperature for 3 hours until it turned clear. The organic layer was separated, dried over sodium sulfate, filtered and concentrated i. vac. The residue was further purified by column chromatography using acetone/hexanes (20%, isocratic) to give the desired product as colorless oil.

1. additionafter completion of addition
2. temperatureThe reaction was cooled back to −78° C.
3. customto quench the excess DiBAl-H
4. additionbefore pouring into 150 mL saturated aqueous Rochelle (sodium potassium tartrate) salts solution
5. stirringThe mixture was vigorously stirred at room temperature for 3 hours until it
6. customThe organic layer was separated
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated i
10. customThe residue was further purified by column chromatography

ORD record

ord-c5f19fb3e2ba442cbf3209efea711df6

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08343990B2