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Tetrahydrofuran → Ethyl 3-dimethylamino-2-(2,4-difluoro-3-methoxybenzoyl)acrylate

HRID 606644
Notes
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Reaction equation

HRID 606644 reaction equation
[F:1][C:2]1[C:10]([O:11][CH3:12])=[C:9]([F:13])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.O1CCC[CH2:15]1.CC1C=CC=[C:37]([N+:41]([O-])=O)C=1C(OC(=O)C1C([N+]([O-])=O)=CC=CC=1C)=O.CN([C:47](=[CH2:53])[C:48]([O:50][CH2:51][CH3:52])=[O:49])C>O.C(N(CC)CC)C>[CH3:15][N:41]([CH3:37])[CH:53]=[C:47]([C:4](=[O:6])[C:3]1[CH:7]=[CH:8][C:9]([F:13])=[C:10]([O:11][CH3:12])[C:2]=1[F:1])[C:48]([O:50][CH2:51][CH3:52])=[O:49]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 37805552,4-Difluoro-3-methoxybenzoic acidHCID 10103284Ethyl dimethylaminoacrylateHCID 104726482-Methyl-6-nitrobenzoic anhydride

Product 1

HCID 67047531Ethyl 3-dimethylamino-2-(2,4-difluoro-3-methoxybenzoyl)acrylate

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 8471TriethylamineSolvent

Procedure

To 376 mg of the 2,4-difluoro-3-methoxybenzoic acid was added 40 mL of tetrahydrofuran. After adding 0.75 ml of triethylamine, 20 mg of N,N-dimethylaminopyridine and 689 mg of 2-methyl-6-nitrobenzoic anhydride to this solution, the mixture was stirred at room temperature. After 2 hours, mixed acid anhydrides were confirmed by TLC, and 430 mg of ethyl N,N-dimethylaminoacrylate was added dropwise thereto. After completion of the dropwise addition, the mixture was stirred for 24 hours. After completion of the reaction, water was added to the reaction mixture, and the separated solution was extracted with ethyl acetate and dried with anhydrous sodium sulfate. After removing the sodium sulfate by filtration, the filtrate was concentration under reduced pressure to obtain 511 mg of a dark brown oily product. The resulting residue was purified by silica gel column chromatography to obtain the title compound.

Workup

  1. additionwas added dropwise
  2. additionAfter completion of the dropwise addition
  3. stirringthe mixture was stirred for 24 hours
  4. additionwas added to the reaction mixture
  5. extractionthe separated solution was extracted with ethyl acetate
  6. dry with materialdried with anhydrous sodium sulfate
  7. customAfter removing the sodium sulfate
  8. filtrationby filtration
  9. concentrationconcentration under reduced pressure

Sources & evidence

ORD record
ord-9bba04e7dd7745a8a606ba1b20ccd3cb
Source dataset
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07915418B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes