Diisobutylaluminumhydride → HCID 90389320, compound

A solution of methyl 5-chloro-2-vinylnicotinate (0.21 g, 1.06 mmol) in DCM (5 ml) was cooled to −45° C. A solution of diisobutylaluminum hydride (1M in hexane, 1.6 ml, 1.59 mmol, Aldrich) was added dropwise. After 15 min, the reaction mixture was quenched by the addition of a saturated aqueous solution of potassium sodium tartrate (3 mL). DCM was added, followed by water. The organic phase was separated, washed with water and dried over MgSO4. The filtrate was concentrated under reduced pressure. The crude material was absorbed onto a plug of silica gel and purified by chromatography, eluting with a gradient of 5% to 55% EtOAc in hexane, to provide the title compound (77 mg) as a white solid. LC/MS m/z=170.1 [M+H]+.

1. customthe reaction mixture was quenched by the addition of a saturated aqueous solution of potassium sodium tartrate (3 mL)
2. additionDCM was added
3. customThe organic phase was separated
4. washwashed with water
5. dry with materialdried over MgSO4
6. concentrationThe filtrate was concentrated under reduced pressure
7. customThe crude material was absorbed onto a plug of silica gel
8. custompurified by chromatography
9. washeluting with a gradient of 5% to 55% EtOAc in hexane

ORD record

ord-8766d17a6ba948ccb4e993a9a7348936

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09085576B2