Potassium methyl malonate → Methyl 4-(4-fluoro-2-methylphenyl)-3-oxobutanoate

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[C:4]([CH3:12])[CH:3]=1.[K+].[CH3:14][O:15][C:16](=[O:21])[CH2:17]C([O-])=O>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=[O:11])[CH2:17][C:16]([O:15][CH3:14])=[O:21])=[C:4]([CH3:12])[CH:3]=1

Participants

Reactant 2

HCID 2724687Potassium methyl malonate

HCID 50169502-(4-Fluoro-2-methylphenyl)acetic acid

Product 1

HCID 86725685Methyl 4-(4-fluoro-2-methylphenyl)-3-oxobutanoateYield 78%

Procedure

The title compound was prepared in 78% yield from 2-(4-fluoro-2-methylphenyl)acetic acid and 3-methoxy-3-oxopropanoic acid potassium salt according to the procedure for the preparation of Example 170, part A. 1H NMR (300 MHz, CDCl3): δ 2.24 (3H, s), 3.47 (2H, s), 3.74 (3H, s), 3.83 (2H, s), 6.88-6.94 (2H, m), 7.07-7.12 (1H, m).

Sources & evidence

ORD record: ord-498890a9175f4b8ab7c2fa2c93d173cb
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987461B2

Reaction notes

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