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5-Formyl-2-methoxy-N-[[4-(trifluoromethyl)phenyl]methyl]-benzamide → Ethyl 2-methoxy-3-[4-methoxy-3-[N-[[4-(trifluoromethyl)phenyl]methyl]carbamoyl]phenyl]acrylate

HRID 1634516
Notes
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Reaction equation

HRID 1634516 reaction equation
C(OP([CH:9]([O:15][CH3:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11])(OCC)=O)C.CC(C)([O-])C.[K+].[F:23][C:24]([F:46])([F:45])[C:25]1[CH:30]=[CH:29][C:28]([CH2:31][NH:32][C:33](=[O:44])[C:34]2[CH:39]=[C:38]([CH:40]=O)[CH:37]=[CH:36][C:35]=2[O:42][CH3:43])=[CH:27][CH:26]=1>O1CCCC1>[CH3:16][O:15][C:9](=[CH:40][C:38]1[CH:37]=[CH:36][C:35]([O:42][CH3:43])=[C:34]([C:33](=[O:44])[NH:32][CH2:31][C:28]2[CH:29]=[CH:30][C:25]([C:24]([F:23])([F:45])[F:46])=[CH:26][CH:27]=2)[CH:39]=1)[C:10]([O:12][CH2:13][CH3:14])=[O:11]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 120946615-Formyl-2-methoxy-N-[[4-(trifluoromethyl)phenyl]methyl]-benzamideHCID 15638229Ethyl 2-(diethoxyphosphoryl)-2-methoxyacetateHCID 23665647Potassium tert-butoxide

Product 1

HCID 69758375Ethyl 2-methoxy-3-[4-methoxy-3-[N-[[4-(trifluoromethyl)phenyl]methyl]carbamoyl]phenyl]acrylateYield 78%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

Procedure

Ethyl 2-(diethoxyphosphoryl)-2-methoxyacetate (265 mg, 1.10 mmol) was dissolved in 3 ml of dehydrated tetrahydrofuran and potassium t-butoxide (123 mg, 1.10 mmol) was added under stirring and cooling with ice under an atmosphere of argon, which was stirred for 30 minutes. Next, N-[[4-(trifluoromethyl)phenyl]methyl]-5-formyl-2-methoxybenzamide (338 mg, 1.00 mmol) dissolved in 2 ml of dehydrated tetrahydrofuran was added. After stirring for 1 hour at room temperature, the reaction mixture was poured into ice water, which was extracted with ethyl acetate, washed with water and brine in sequence, then dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel chromatography (eluate n-hexane:ethyl acetate=3:1 v/v) to obtain 330 mg (78%) of the title compound (mixture of geometrical isomers relevant to double bond) as colorless crystals.

Workup

  1. temperaturecooling with ice under an atmosphere of argon
  2. stirringwhich was stirred for 30 minutes
  3. additionwas added
  4. stirringAfter stirring for 1 hour at room temperature
  5. extractionwas extracted with ethyl acetate
  6. washwashed with water and brine in sequence
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel chromatography (eluate n-hexane:ethyl acetate=3:1 v/v)

Sources & evidence

ORD record
ord-8c95901993cd43b3a668054fa84c23d8
Source dataset
uspto-grants-2003_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06506797B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes