Diethyl Malonate → HCID 86675065, compound

HRID 1519403Notes

Reaction equation

HRID 1519403 reaction equation
[OH:1][C:2]1[C:9]([CH2:10][CH3:11])=[C:8]([O:12][CH3:13])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[C:14](OCC)(=[O:21])[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].N1CCCCC1>C(O)C>[CH2:19]([O:18][C:16]([C:15]1[C:14](=[O:21])[O:1][C:2]2[C:3]([CH:4]=1)=[CH:6][CH:7]=[C:8]([O:12][CH3:13])[C:9]=2[CH2:10][CH3:11])=[O:17])[CH3:20]

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 8082PiperidineHCID 84657285HCID 84657285, compound

Product 1

HCID 86675065HCID 86675065, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-hydroxy-4-methoxy-3-ethyl-benzaldehyde (3.1 g, 17.2 mmol) in ethanol (93 mL) is added diethyl malonate (2.8 g, 17.2 mmol) and piperidine (1.5 g, 17.2 mmol). The reaction mixture was stirred at room temperature overnight. The reaction mixture was then cooled to 0° C. with ice/water bath and the formed precipitate was filtered and washed with ethanol to give 7-methoxy-2-oxo-8-ethyl-2H-chromene-3-carboxylic acid ethyl ester (3.1 g, 65%).

Workup

  1. temperatureThe reaction mixture was then cooled to 0° C. with ice/water bath
  2. filtrationthe formed precipitate was filtered
  3. washwashed with ethanol

Sources & evidence

ORD record
ord-0d6c0ce5be3048b595255c65a37abf18
Source dataset
uspto-grants-2015_07
Patent number
US09073888B2

Reaction notes

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