Toluene → HCID 12641374, compound

Temperature

-78 °C

A solution of 1M DIBAL-H in toluene (125.0 mL, 125 mmol) was slowly added over a period of 10 mins, to a solution of diethylmalonate (10.0 mL, 62.5 mmol, (4)) in Et2O (13.6 mL) at −78° C. under N2. The internal temperature was maintained −78° C. The mixture was stirred for 1 h at −78° C. A solution of hexylmagnesium bromide in Et2O (65.0 mL, 130 mmol) was added at −78° C. The reaction mixture was then warmed to room temperature and stirred for 6 h. The mixture was quenched with saturated NH4Cl solution at 0° C. A saturated solution of Rochelle's salt was added at room temperature and the two-phase mixture was stirred for approximately 8 h. The aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over Na2SO4. The solvent was removed in vacuum, and the resulting material was purified via column chromatography (30% Ethyacetate-70% hexanes) to provide the desired product (6.4 g, 42%, (10)).

1. temperatureThe reaction mixture was then warmed to room temperature
2. stirringstirred for 6 h
3. customThe mixture was quenched with saturated NH4Cl solution at 0° C
4. additionA saturated solution of Rochelle's salt was added at room temperature
5. stirringthe two-phase mixture was stirred for approximately 8 h
6. extractionThe aqueous layer was extracted with ethyl acetate
7. dry with materialThe combined organic layers were dried over Na2SO4
8. customThe solvent was removed in vacuum
9. customthe resulting material was purified via column chromatography (30% Ethyacetate-70% hexanes)

ORD record

ord-9588c134b1274642b05db63c51041d4f

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08822635B2