ChemicalBook CAS DataBase List Diethyl 1H-pyrrole-2,4-dicarboxylate

Diethyl 1H-pyrrole-2,4-dicarboxylate synthesis

15synthesis methods

Product Name:Diethyl 1H-pyrrole-2,4-dicarboxylate
CAS Number:55942-40-0
Molecular formula:C10H13NO4
Molecular Weight:211.21

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55942-40-0
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Yield: 38%

Reaction Conditions:

with formaldehyd;1,8-diazabicyclo[5.4.0]undec-7-ene in tetrahydrofuran

Steps:

403 403A-Preparation of 2,4-dicarboethoxypyrrole
403A-Preparation of 2,4-dicarboethoxypyrrole To a stirred solution of ethyl isocyanoacetate (0.02 mol, 2.3 mL) and DBU (3.0 g, 0.02 mol) in THF (30 mL) was added a solution of formaldehyde (0.6M THF solution, 16.6 mL, 0.01 mole) at 45-50° C. for a period of 15 min. After stirring for 5 hr at the same temperature, the reaction mixture was neutralized with HOAc and the solvents were removed under reduced pressure. The resulting oil was partitioned between satd. aq. NaHCO₃ and EtOAc. The EtOAc layer was separated, dried with Na₂SO₄ and concentrated in vacuo to obtain a viscous oil which was chromatographed on silica (20% EtOAc-hexanes) to give 403A (0.80 g, 38%). MS Found: (M+H)⁺=212.0; ¹H NMR (CDCl₃) δ 9.8 (br, 1H), 7.56 (dd, J₁=3.2 Hz, J₂=1.5 Hz, 1H), 7. (dd, J₁=3.2 Hz, J₂=1.5 Hz, 1H), 4.3 (m, 4H), 1.3 (m, 6H).

References:

Salvati, Mark E.;Illig, Carl R.;Wilson, Kenneth Jerome;Chen, Jinsheng;Meegalla, Sanath K.;Wall, Mark James US2004/209886, 2004, A1

2999-46-4
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$13.43/1gm: