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

HRID 8470
Notes
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Reaction equation

HRID 8470 reaction equation
CC(C)([O-])C.[K+].[F:7][C:8]1[C:18]([F:19])=[C:17]([F:20])[CH:16]=[CH:15][C:9]=1[NH:10][C@@H:11]([CH3:14])[CH2:12][OH:13].C(O[CH:24]=[C:25]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:26]([O:28][CH2:29][CH3:30])=[O:27])C>CN(C=O)C>[F:7][C:8]1[C:18]([F:19])=[C:17]([F:20])[CH:16]=[CH:15][C:9]=1[N:10]([CH:24]=[C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:31]([O:33][CH2:34][CH3:35])=[O:32])[C@@H:11]([CH3:14])[CH2:12][OH:13]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6871Diethyl (ethoxymethylene)malonateHCID 11401466(2S)-2-(2,3,4-Trifluoroanilino)propanolHCID 23665647Potassium tert-butoxide

Product 1

HCID 11485652Diethyl [2,3,4-trifluoro[(1S)-2-hydroxy-1-methylethyl]anilino]methylenemalonateYield 75%

Reagents, catalysts & solvents 1

HCID 6228Dimethylformamide
Solvent
2×

Conditions

Temperature
0 °C

Procedure

Potassium tertiary-butoxide (62 mg) was added to DMF (2 ml) and cooled to 0° C. Then a solution of the compound (100 mg) obtained in Example 51 in DMF (200 μl) was dropped therein to. After stirring for 15 minutes, diethyl ethoxymethylenemalonate was dropped therein to and the resultant mixture was stirred for 8 hours at room temperature. After treating in a conventional manner, it was subjected to silica gel column chromatography to thereby give 137 mg (75%) of the title compound as a colorless solid. The 1H-NMR and IR spectral data of this product was identical with those of the compound obtained in Example 63.

Workup

  1. additionAfter treating in a conventional manner, it

Sources & evidence

ORD record
ord-c96adb10928b41d7981fb57fdafcfa77
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07087778B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes