Diisopropylamine → HCID 86617051, compound

Temperature

-20 °C

nButyllithium (2.5 M, 7.9 ml, 19.76 mmol) was added at −20° C. to a solution of di-iso-propylamine (3.29 ml, 23.24 mmol) in tetrahydrofuran (40 ml). The reaction mixture was stirred for 15 minutes under nitrogen at −20° C. then the mixture was allowed to cool down to −78° C. tert-Butylacetate (2.64 ml, 19.67 mmol) was added and the mixture was stirred at −78° C. for 20 minutes. A solution of ethyl 4-phenoxybenzoate (2.17 g, 8.94 mmol) in tetrahydrofuran (5 ml) was further added to this and the resulting mixture was stirred at −78° C. for 50 minutes. A saturated solution of NH4Cl was added and the whole was extracted with EtOAc. The organics were dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with 8% Et2O in petroleum ether to afford the title compound as a colourless oil (1.53 g, 55% yield). MS (ES+) m/e=313. 1H NMR (CDCl3) δH 1.47 (9H, s), 3.88 (2H, s), 7.02 (2H, d), 7.10 (2H, d), 7.24 (1H, t), 7.43 (2H, t), 7.94 (2H, d).

1. additionwas added
2. stirringthe mixture was stirred at −78° C. for 20 minutes
3. stirringwas stirred at −78° C. for 50 minutes
4. extractionthe whole was extracted with EtOAc
5. dry with materialThe organics were dried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe residue was purified by silica gel chromatography
9. washeluting with 8% Et2O in petroleum ether

ORD record

ord-dbdc4554dde7482c9c5767ba429f459a

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07589214B2