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Water → HCID 54452402, compound

HRID 1073110
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Reaction equation

HRID 1073110 reaction equation
[CH3:1][C:2]1[C:7]([C:8](OC)=[O:9])=[C:6]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[C:5]([C:19](OC)=[O:20])=[C:4]([CH3:23])[N:3]=1.O>C1(C)C=CC=CC=1.O1CCCC1>[OH:9][CH2:8][C:7]1[C:2]([CH3:1])=[N:3][C:4]([CH3:23])=[C:5]([CH2:19][OH:20])[C:6]=1[C:12]1[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 962WaterHCID 735523Dimethyl 4-(4-fluorophenyl)-2,6-dimethylpyridine-3,5-dicarboxylate

Product 1

HCID 54452402HCID 54452402, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

25 ml (87.5 mmol) of a 3.5 molar solution of sodium bis-(2-methoxyethoxy)-dihydroaluminate in toluene are added under nitrogen to a solution of 7.9 g (25 mmol) of the compound from Example 19 in 100 ml of dry tetrahydrofuran at 0° C. The mixture is stirred at room temperature for 6 h, cooled again to 0° C. and 200 ml of water are slowly added dropwise. The mixture is extracted three times using 150 ml of ethyl acetate each time, the combined organic phases are washed once with saturated sodium chloride solution, dried over magnesium sulphate and concentrated in vacuo. The residue is stirred with ether, filtered off with suction and dried in a desiccator.

Workup

  1. temperaturecooled again to 0° C.
  2. extractionThe mixture is extracted three times
  3. washthe combined organic phases are washed once with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated in vacuo
  6. stirringThe residue is stirred with ether
  7. filtrationfiltered off with suction
  8. customdried in a desiccator

Sources & evidence

ORD record
ord-558485550ebc40ad953be51765d4632d
Source dataset
uspto-grants-1990_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04968689

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes