ChemicalBook CAS DataBase List 2-(Diethylamino)-ethyl acrylate

2-(Diethylamino)-ethyl acrylate synthesis

5synthesis methods

Product Name:2-(Diethylamino)-ethyl acrylate
CAS Number:2426-54-2
Molecular formula:C9H17NO2
Molecular Weight:171.24

Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-

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Yield: 93%

Reaction Conditions:

with 2-chloro-4,6-dimethoxy-1 ,3,5-triazine;triethylamine in dichloromethane at 20; for 0.25 h;Eschenmoser Methylenation;

Steps:

synthesis of2-(diethylamino)ethyl acrylate (3e)
To a solution of 2-(diethylamino)ethyl 3-(dimethylamino)propionate 1e (56.0 mg, 0.263 mmol) in CH₂Cl₂ (1.3 mL) were added CDMT (47.0 mg, 0.263 mmol, 1.0 eq.) and Et₃N (36.0 μL, 0.263 mmol, 1.0 eq.) at room temperature. After being stirred for 15 minutes, the reaction mixture was directly loaded on silica gel column chromatography, and eluted with dichloromethane: methanol = 15:1 to obtain 3e (43.0 mg, 93 %). ¹H NMR (CDCl₃) d 6.41 (dd, J = 1.1, 10 Hz, 1H), 6.14 (dd, J = 10, 17 Hz, 1H), 5.82 (dd, J = 1.1, 10 Hz, 1H), 4.23 (t, J = 6.2 Hz, 2H), 2.75(t, J = 6.2 Hz, 2H), 2.59 (q, J = 7.0 Hz, 4H), 1.04 (t, J = 7.0 Hz, 6H);¹³C NMR (CDCl₃)d 166.3, 130.7, 128.5, 62.9, 50.9, 47.7, 11.9; IR (CHCl₃) cm^-1: 3049, 2962, 1730, 1707, 1637, 1620, 1408, 1296, 1279, 1178, 1060, 984, 970; LRMS (ESI-MS): 172 ([M+H]⁺ ).

References:

Yamada, Kohei;Masaki, Kazumasa;Hagimoto, Yuri;Kamiya, Seina;Kunishima, Munetaka [Tetrahedron Letters,2013,vol. 54,# 13,p. 1758 - 1760] Location in patent:supporting information