p-Toluenesulfonyl azide → 2-Diazo-3-oxobutyroxyethyl methacrylate

Temperatur

0 °C

2-Diazo-3-oxobutyroxyethyl methacrylate monomer was prepared as follows: a mixture of 2-acetoacetoxyethyl methacrylate (4.28 gm, 20 mmol, available from Eastman Chemical, Kingsport, Tenn.), dichloromethane (30 ml), and p-toluenesulfonyl azide (3.94 gm, 20 mmol) was cooled to 0° C. and then DBU (1,8-diazabicyclo[5.4.0]undec-7-ene, 4.48 ml, 30 mmol) was added dropwise. After the addition of DBU, the reaction mixture was stirred at room temperature for 15 minutes and then poured into a mixture of 10% KOH (100 ml) and diethyl ether (50 ml). The organic layer was separated and the aqueous layer was re-extracted with diethyl ether (50 ml). The organic extracts were combined and then washed sequentially with 3N HCl (50 ml), deionized water (2×50 ml) and saturated aqueous sodium chloride solution (50 ml). The organic layer was dried using anhydrous magnesium sulfate, filtered, and concentrated to give 4.39 gm of 2-diazo-3-oxobutyroxyethyl methacrylate as a pale yellow oil. 1H NMR (400 MHz, CDCl3): δ 1.94 (s, 3H); 2.47 (s, 3H); 4.35-4.55 (m, 4H); 5.60 (s, 1H); 6.12 (s, 1H). IR: 2181 cm-1. Peak decomposition temperature: 156° C. (by DSC).

1. custom2-Diazo-3-oxobutyroxyethyl methacrylate monomer was prepared
2. customThe organic layer was separated
3. extractionthe aqueous layer was re-extracted with diethyl ether (50 ml)
4. washwashed sequentially with 3N HCl (50 ml), deionized water (2×50 ml) and saturated aqueous sodium chloride solution (50 ml)
5. customThe organic layer was dried
6. filtrationfiltered
7. concentrationconcentrated

ORD-Eintrag

ord-e26c55e3d5414344905f4827505a43df

Quelldatensatz

uspto-grants-1998_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05747217