Ethyl Acetoacetate → Ethyl 2-[(6-fluoro-2-methyl-4-oxo-4H-chromen-8-yl)methylene]-3-oxobutanoate

HRID 557422Notes

Reaction equation

HRID 557422 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH:12]=O)[CH:11]=1)[O:8][C:7]([CH3:14])=[CH:6][C:5]2=[O:15].[C:16]([O:22][CH2:23][CH3:24])(=[O:21])[CH2:17][C:18]([CH3:20])=[O:19]>>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH:12]=[C:17]([C:18](=[O:19])[CH3:20])[C:16]([O:22][CH2:23][CH3:24])=[O:21])[CH:11]=1)[O:8][C:7]([CH3:14])=[CH:6][C:5]2=[O:15]

Participants

3

Reactant 2

HCID 8868Ethyl AcetoacetateHCID 578286506-Fluoro-2-methyl-4-oxo-4H-1-benzopyran-8-carbaldehyde

Product 1

HCID 66991191Ethyl 2-[(6-fluoro-2-methyl-4-oxo-4H-chromen-8-yl)methylene]-3-oxobutanoate

Procedure

The title compound is prepared in analogy to example 25 (stage 25a) starting from 6-fluoro-2-methyl-4-oxo-4H-chromene-8-carbaldehyde (2.18 g, 10.62 mmol) and ethyl acetoacetate (1.33 g, 10.62 mmol). 3.30 g (98% of theory) of the title compound are obtained as an E/Z isomer mixture.

Workup

  1. customThe title compound is prepared in analogy to example 25 (stage 25a)

Sources & evidence

ORD record
ord-9ce9a6eda12745f59bfd59ad0e46452c
Source dataset
uspto-grants-2011_11
Patent number
US08058447B2

Reaction notes

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