Diethyl methylmalonate → HCID 60155535, compound

HRID 1506876Notes

Reaction equation

HRID 1506876 reaction equation
[F:1][C:2]1[CH:7]=[C:6](F)[C:5]([F:9])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[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:5]1[CH:4]=[C:3]([N+:10]([O-:12])=[O:11])[C:2]([F:1])=[CH:7][C:6]=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 750121,2,4-Trifluoro-5-nitrobenzene

Product 1

HCID 60155535HCID 60155535, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of commercially available 2,4,5-trifluoro-nitrobenzene (25a) (5.0 mL, 43.5 mmol), diethyl methylmalonate (6.2 mL, 36.1 mmol), and sodium hydroxide (1.57 g, 39.1 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 11.0 g (76%) of compound (26a) 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-6b82b46992734800ad35693235e56837
Source dataset
uspto-grants-2015_12
Patent number
US09221786B2

Reaction notes

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