Dimethyl malonate → HCID 21925692, compound

HRID 1057465Notes

Reaction equation

HRID 1057465 reaction equation
[C:1]([O:8][CH3:9])(=[O:7])[CH2:2][C:3]([O:5][CH3:6])=[O:4].[H-].[Na+].F[C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([NH:25][C:26](=[O:31])[C:27]([F:30])([F:29])[F:28])[CH:20]=2)=[CH:15][C:14]=1[N+:32]([O-:34])=[O:33].CCCCCC>CS(C)=O>[N+:32]([C:14]1[CH:15]=[C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([NH:25][C:26](=[O:31])[C:27]([F:28])([F:29])[F:30])[CH:20]=2)[CH:17]=[CH:18][C:13]=1[CH:2]([C:1]([O:8][CH3:9])=[O:7])[C:3]([O:5][CH3:6])=[O:4])([O-:34])=[O:33]

Participants

6

Reactant 4

HCID 7943Dimethyl malonateHCID 8058HexaneHCID 24758Sodium hydrideHCID 21925694HCID 21925694, compound

Product 1

HCID 21925692HCID 21925692, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
100 °C

Procedure

Dimethyl malonate (9.6 mL) was added dropwise to a stirred suspension of 3.2 g of 60% sodium hydride in mineral oil in 40 mL of anhydrous dimethylsulfoxide under nitrogen. The mixture was stirred for 10 minutes and 2-fluoro-5-(3-trifluoroacetamidophenyl)nitrobenzene in 20 mL of dimethylsulfoxide was added. The resulting dark red mixture was heated to 100° C. for 2 hours. The reaction was quenched by pouring into 100 mL of saturated ammonium chloride solution and extracted twice with 50 mL of ethyl acetate each time. The organic phase was washed with 50 mL each of saturated ammonium chloride solution, water, and brine, dried over anhydrous sodium sulfate and concentrated to a yellow oil. The oil was chromatographed on a column of silica gel eluting with a 1:4 mixture of ethyl acetate:hexane to give 4.4 g (50% yield) of dimethyl 2-[2-nitro-4-(3-trifluoroacetamidophenyl)phenyl]malonate as a pale yellow solid.

Workup

  1. customThe reaction was quenched
  2. additionby pouring into 100 mL of saturated ammonium chloride solution
  3. extractionextracted twice with 50 mL of ethyl acetate each time
  4. washThe organic phase was washed with 50 mL each of saturated ammonium chloride solution, water, and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated to a yellow oil
  7. customThe oil was chromatographed on a column of silica gel eluting with a 1:4 mixture of ethyl acetate

Sources & evidence

ORD record
ord-22181069b7624938b6cbc96484472160
Source dataset
uspto-grants-2003_02
Patent number
US06514981B1

Reaction notes

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