Diethyl (ethoxymethylene)malonate → Diethyl [2,3,4-trifluoro[(1S)-2-hydroxy-1-methylethyl]anilino]methylenemalonate

HRID 458200

Reaction equation

HRID 458200 reaction equation
[F:1][C:2]1[C:12]([F:13])=[C:11]([F:14])[CH:10]=[CH:9][C:3]=1[NH:4][C@@H:5]([CH3:8])[CH2:6][OH:7].C(O[CH:18]=[C:19]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:20]([O:22][CH2:23][CH3:24])=[O:21])C.C(=O)([O-])[O-].[K+].[K+]>[Cl-].C([N+](CCCCCC)(CCCCCC)CCCCCC)CCCCC.CC(C)=O>[F:1][C:2]1[C:12]([F:13])=[C:11]([F:14])[CH:10]=[CH:9][C:3]=1[N:4]([CH:18]=[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:25]([O:27][CH2:28][CH3:29])=[O:26])[C@@H:5]([CH3:8])[CH2:6][OH:7]

Participants

6

Reactant 3

HCID 6871Diethyl (ethoxymethylene)malonateHCID 11430Potassium CarbonateHCID 11401466(2S)-2-(2,3,4-Trifluoroanilino)propanol

Product 1

HCID 11485652Diethyl [2,3,4-trifluoro[(1S)-2-hydroxy-1-methylethyl]anilino]methylenemalonateYield 84%

Reagents, catalysts & solvents 2

HCID 80021Tetrahexylammonium chlorideCatalystHCID 180AcetoneSolvent

Procedure

The compound (300 mg) obtained in Example 51, diethyl ethoxymethylenemalonate (632 mg) and tetrahexylammonium chloride (57 mg) were dissolved in acetone (3 ml). After adding potassium carbonate (445 mg), the mixture was stirred at room temperature for 4.5 hours. After the completion of the reaction, the solvent was evaporated. Then the residue thus obtained was subjected to silica gel column chromatography to thereby give 338 mg (84%) of the title compound as a colorless solid.

Workup

  1. customAfter the completion of the reaction
  2. customthe solvent was evaporated
  3. customThen the residue thus obtained

Sources & evidence

ORD record
ord-7d56f22b88114b1f99466e1d7e97dff2
Source dataset
uspto-grants-2007_03
Patent number
US07189847B2

Linked notes

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