tert-Butanol → Diethyl 2-acetamido-2-(4-tetradecenyl)malonate

Temperature

-78 °C

Decyltriphenylphosphonium bromide (10.85 g) was dissolved in 100 ml of dry tetrahydrofuran. Under an argon atmosphere, 13 ml of a 1.6 M n-butyl lithium/hexane solution was dropwise added thereto and the mixture was stirred for 15 minutes. The mixture was cooled to -78° C. and a solution of diethyl 2-acetamido-2-(4-formylbutyl)malonate (4.17 g)/dry tetrahydrofuran (50 ml) was dropwise added thereto and the mixture was stirred at 78° C. for 40 minutes under an argon atmosphere. Under the same conditions, a solution of t-butanol (3.3 ml)/tetrahydrofuran (15 ml) was dropwise added thereto and the mixture was stirred at room temperature under an argon atmosphere for 1.5 hours. The reaction mixture was diluted with ether and washed with water. The organic layer was dried and concentrated. The concentrate was purified by silica gel column chromatography using hexane-acetic acid (5:1→5:2) as an eluent to give 2.1 g of colorlegs, oily diethyl 2-acetamido-2-(4-tetradecenyl)malonate.

1. stirringthe mixture was stirred at 78° C. for 40 minutes under an argon atmosphere
2. stirringthe mixture was stirred at room temperature under an argon atmosphere for 1.5 hours
3. washwashed with water
4. customThe organic layer was dried
5. concentrationconcentrated
6. customThe concentrate was purified by silica gel column chromatography

ORD record

ord-f969579b2fbe4260afbf32943f0e5b37

Source dataset

uspto-grants-1998_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05719176