Diethyl methylmalonate → HCID 58280423, compound

HRID 1506877Notes

Reaction equation

HRID 1506877 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N+:10]([O-:12])=[O:11])[CH:5]=[C:6]([F:9])[C:7]=1F.[CH3:13][CH:14]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16].[OH-].[Na+]>CN(C=O)C>[F:9][C:6]1[CH:5]=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=[C:2]([F:1])[C:7]=1[C:14]([CH3:13])([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:20]([O:22][CH2:23][CH3:24])=[O:21]

Participants

5

Reactant 3

HCID 11857Diethyl methylmalonateHCID 14798Sodium HydroxideHCID 27827931,2,3-Trifluoro-5-nitrobenzene

Product 1

HCID 58280423HCID 58280423, compoundYield 76.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of commercially available 3,4,5-trifluoro-nitrobenzene (25b) (5.0 mL, 42.8 mmol), diethyl methylmalonate (6.1 mL, 35.7 mmol), and sodium hydroxide (1.54 g, 38.5 mmol) in DMF (55 mL) was allowed to react in the same manner as in (a) in Production Example 1. The crude product was subjected to silica gel column chromatography and elution with an n-hexane/ethyl acetate (10:1) solution to give 9.1 g (63%) of compound (26b) of interest as clear brown oil.

Workup

  1. washThe crude product was subjected to silica gel column chromatography and elution with an n-hexane/ethyl acetate (10:1) solution

Sources & evidence

ORD record
ord-14129075846a4110b3e616f7e63c679b
Source dataset
uspto-grants-2015_12
Patent number
US09221786B2

Reaction notes

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