Hydrochloric Acid → Tert-butyl 5-biphenyl-4-yl-3-oxopentanoate

A solution of tert-butyl acetoacetate (7.2 g) in tetrahydrofuran (80 ml) was added to a stirred solution of sodium hydride (1.33 g) in tetrahydrofuran (60 ml) at 0° C. under nitrogen atmosphere. The reaction mixture was stirred for 10 minutes followed by the addition of n-butyl lithium (23 ml, 2.5 M solution in hexane) dropwise over 10 minutes. The resulting reaction mixture was stirred for 10 minutes. A solution of 4-(bromomethyl) biphenyl (12.5 g) in tetrahydrofuran (60 ml) was added over 10 minutes and the resulting solution was stirred at 0° C. for approximately 2 hours. To resulting mixture was added hydrochloric acid (6 M, 15 ml) followed by extracting the mixture with diethyl ether. The organic layers were combined, washed with water and brine and dried over anhydrous sodium sulphate. The solvent was evaporated under reduced pressure and the residue thus obtained was purified by silica gel column chromatography using 8% ethyl acetate-hexane as eluant to furnish the title compound (7.5 g).

1. customThe resulting reaction mixture
2. stirringwas stirred for 10 minutes
3. stirringthe resulting solution was stirred at 0° C. for approximately 2 hours
4. customTo resulting mixture
5. extractionby extracting the mixture with diethyl ether
6. washwashed with water and brine
7. dry with materialdried over anhydrous sodium sulphate
8. customThe solvent was evaporated under reduced pressure
9. customthe residue thus obtained
10. customwas purified by silica gel column chromatography

ORD record

ord-20ee7ed2e6d4424fb351a213790e2d5b

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08710261B2