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Dimethylformamide → Ethyl 2-methyl-3-(4-methylphenyl)-2-propenoate

HRID 29116
Notes
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Reaction equation

HRID 29116 reaction equation
CN(C)C=O.CC(C)([O-])C.[Na+].[CH3:12][CH2:13][O:14][C:15]([CH:17](P(OCC)(OCC)=O)[CH3:18])=[O:16].[CH3:27][C:28]1[CH:35]=[CH:34][C:31]([CH:32]=O)=[CH:30][CH:29]=1>O>[CH3:18][C:17](=[CH:32][C:31]1[CH:34]=[CH:35][C:28]([CH3:27])=[CH:29][CH:30]=1)[C:15]([O:14][CH2:13][CH3:12])=[O:16]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 77254-MethylbenzaldehydeHCID 107155Triethyl 2-phosphonopropionateHCID 23676156Sodium t-butoxide

Product 1

HCID 68712312Ethyl 2-methyl-3-(4-methylphenyl)-2-propenoateYield 98.8%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Conditions

Temperature
-2.5 °C

Procedure

To dimethylformamide (1802 ml) that had been cooled to −10° C. was added sodium tert-butoxide (528.6 g) and the solution was stirred at −5 to 0° C. for 30 min. Triethyl 2-phosphonopropionate (1310 g) was added dropwise thereto at 10° C. or below. The solution was stirred at 2 to 5° C. for 1 hr, and 4-methylbenzaldehyde (600.8 g) was added dropwise thereto at 10° C. or below and the solution was stirred at room temperature for 1 hr. Water was added thereto and the solution was extracted with toluene. The extract was washed with water and the solvent was distilled off to give the title compound as an oil (1009 g, yield 98.8%).

Workup

  1. customat 10° C. or below
  2. stirringThe solution was stirred at 2 to 5° C. for 1 hr
  3. stirringat 10° C. or below and the solution was stirred at room temperature for 1 hr
  4. extractionthe solution was extracted with toluene
  5. washThe extract was washed with water
  6. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-2eb2a4dd9a0740a3b26f8005a0b593f5
Source dataset
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07420070B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes