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

Temperatur

-78 °C

Decyltriphenylphosphonium bromide (10.85 g) was dissolved in 100 ml of dry tetrahydrofuran. Under an argon atmosphere, 13 ml of a 1.6M 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 dehydrated 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 colorless, 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. concentrationconcentrated
5. customThe concentrate was purified by silica gel column chromatography

ORD-Eintrag

ord-a4474a4507744448a09cea27aba2cb7c

Quelldatensatz

uspto-grants-1999_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05952316