Aluminium lithium hydride → HCID 66761660, compound

Temperature

0 °C

To a solution of tert-butyl 2-chloro-5-(2-methoxyethyl)benzoate from the previous step (1 eq.) in anhydrous THF (0.26 M) was added, at 0° C., lithium aluminum hydride (1.0 M THF solution, 3 eq.). The resulting suspension was stirred at 0° C. for 1 h and then at RT for 1 h. After carefully quenching with EtOAc and H2O, sat. aq. sodium potassium tartrate was added. The resulting biphasic mixture was vigorously stirred at RT for 30 min and then extracted with ether. The combined organic extracts were washed with brine, dried over MgSO4 and filtered. Concentration of the filtrate in vacuo afforded a cloudy oil. Purification of the crude product thus obtained by way of flash chromatography (SiO2, 90:10→70:30 (v/v) Hex:EtOAc) afforded the title compound as a colorless oil.

1. waitat RT for 1 h
2. customAfter carefully quenching with EtOAc and H2O, sat. aq. sodium potassium tartrate
3. additionwas added
4. stirringThe resulting biphasic mixture was vigorously stirred at RT for 30 min
5. extractionextracted with ether
6. washThe combined organic extracts were washed with brine
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. customConcentration of the filtrate in vacuo afforded a cloudy oil
10. customPurification of the crude product
11. customthus obtained by way of flash chromatography (SiO2, 90:10→70:30 (v/v) Hex:EtOAc)

ORD record

ord-05960729684f4b7d91386fedbbd58fb7

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08063105B2