Diethyl Malonate → HCID 18404089, compound

HRID 1017720Notes

Reaction equation

HRID 1017720 reaction equation
C1(P(=[N:20][C:21]2[CH:25]=[CH:24][S:23][C:22]=2[CH:26]=O)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:28]([O:36][CH2:37][CH3:38])(=[O:35])[CH2:29][C:30]([O:32][CH2:33][CH3:34])=O.N1CCCCC1>CCO>[CH2:33]([O:32][C:30]1[N:20]=[C:21]2[CH:25]=[CH:24][S:23][C:22]2=[CH:26][C:29]=1[C:28]([O:36][CH2:37][CH3:38])=[O:35])[CH3:34]

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 8082PiperidineHCID 18404100HCID 18404100, compound

Product 1

HCID 18404089HCID 18404089, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-[(triphenylphosphoranylidene)amino]-2-thiophenecarbaldehyde (11-2, 2.50 g, 6.45 mmol, 1 equiv), diethyl malonate (1.96 mL, 12.9 mmol, 2.00 equiv), and piperidine (0.319 mL, 3.23 mmol, 0.500 equiv) in EtOH (50 mL) was heated at reflux for 16 h. The reaction mixture was concentrated, and the residue was purified by flash column chromatography (heaxane, initally, grading to 30% EtOAc in hexane) to give ethyl 5-ethoxythieno[3,2-b]pyridine-6-carboxylate (11-3) as an off-white solid. 1H NMR (300 MHz, CDCl3) δ 8.64 (s, 1H), 7.84 (d, 1H, J=7.4 Hz), 7.37 (d, 1H, J=7.2 Hz), 4.55 (q, 2H, J=7.0 Hz), 4.40 (q, 2H, J=7.1 Hz), 1.48 (t, 3H, J=7.0 Hz), 1.41 (t, 3H, J=7.1 Hz).

Workup

  1. temperatureat reflux for 16 h
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was purified by flash column chromatography (heaxane

Sources & evidence

ORD record
ord-514c30beeeae4b94b41ee5759dd498b8
Source dataset
uspto-grants-2002_11
Patent number
US06479512B1

Reaction notes

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