Water → HCID 15841100, compound

HRID 1418594Notes

Reaction equation

HRID 1418594 reaction equation
[CH3:1][N:2]([CH3:15])[C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[C:10](\[CH3:14])/[C:11]([OH:13])=[O:12])=[CH:5][CH:4]=1.[CH2:16]([Li])[CH2:17]CC.CN(C)C1C=CC(C=O)=CC=1.O>CCCCCC>[CH3:15][N:2]([CH3:1])[C:3]1[CH:4]=[CH:5][C:6](/[CH:9]=[C:10](\[CH3:14])/[C:11]([O:13][CH2:16][CH3:17])=[O:12])=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 74794-(Dimethylamino)BenzaldehydeHCID 5388693HCID 5388693, compoundHCID 178418339Butyllithium

Product 1

HCID 15841100HCID 15841100, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

E-3-(4-Dimethylaminophenyl)-2-methyl-propenoic acid guanidide hydrochloride ##STR6## 1 a) 1 eq. of triethyl phosphonopropionate was deprotonated with 1 eq. of n-butyllithium in hexane at 0° C., and 1 eq. of 4-dimethylaminobenzaldehyd was then added at RT. After the aldehyde had reacted completely, the mixture was worked up with water and extracted three times by shaking with toluene. After the combined organic phases had been dried over magnesium sulfate, the solvent was removed in vacuo and the crude product which remained was separated by chromatography over silica gel using EA/HEP mixtures as the eluent. Ethyl E-3-(4-dimethylamino-phenyl)-2-methyl-acrylate was isolated. orange-yellowish oil MS 233 (M+)

Workup

  1. extractionextracted three times
  2. dry with materialAfter the combined organic phases had been dried over magnesium sulfate
  3. customthe solvent was removed in vacuo
  4. customthe crude product which remained was separated by chromatography over silica gel

Sources & evidence

ORD record
ord-3df15af2c95747bfbae57f42f3a6f667
Source dataset
uspto-grants-1999_03
Patent number
US05883133

Reaction notes

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