1,1,3,3-Tetramethylguanidine → Ethyl 3-[4-(benzyloxy)phenyl]-2-ethoxyprop-2-enoate

HRID 987269Notes

Reaction equation

HRID 987269 reaction equation
CN(C)C(=N)N(C)C.[CH2:9]([O:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Cl-].[CH2:26]([O:28][CH:29]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH3:27]>C(Cl)(Cl)Cl>[CH2:33]([O:32][C:30](=[O:31])[C:29]([O:28][CH2:26][CH3:27])=[CH:21][C:20]1[CH:23]=[CH:24][C:17]([O:16][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:18][CH:19]=1)[CH3:34]

Participants

5

Reactant 3

HCID 664601,1,3,3-TetramethylguanidineHCID 78109Benzaldehyde, 4-(phenylmethoxy)-HCID 11327835Phosphonium, (1,2-diethoxy-2-oxoethyl)triphenyl-, chloride (1:1)

Product 1

HCID 54423854Ethyl 3-[4-(benzyloxy)phenyl]-2-ethoxyprop-2-enoateYield 85.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Tetramethylguanidine (42.3 g; 0.37 mole) was slowly added to a solution of 4-benzyloxybenzaldehyde (75.6 g; 0.36 mole) and (1,2-diethoxy-2-oxoethyl) (triphenyl)phosphonium chloride (130.7 g; 0.304 mole) dissolved in chloroform (800 ml) at 0° C. After stirring at room temperature over night, the solvent was evaporated in vacuo. The residue was dissolved in diethyl ether, insoluble material was filtered off and the filtrate was washed with sodium bicarbonate and dried (magnesium sulfate). The procedure was repeated once and thereafter the crude product was stirred over night with a sodium bisulfite saturated water solution. The solid material was filtered off, the product was extracted with diethyl ether, dried (magnesium sulfate) and the solvent was evaporated in vacuo to give 85 g (yield 73%) of 3-(4-benzyloxyphenyl)-2-ethoxyacrylic acid ethyl ester.

Workup

  1. customthe solvent was evaporated in vacuo
  2. dissolutionThe residue was dissolved in diethyl ether
  3. filtrationinsoluble material was filtered off
  4. washthe filtrate was washed with sodium bicarbonate
  5. dry with materialdried (magnesium sulfate)
  6. stirringthe crude product was stirred over night with a sodium bisulfite saturated water solution
  7. filtrationThe solid material was filtered off
  8. extractionthe product was extracted with diethyl ether
  9. dry with materialdried (magnesium sulfate)
  10. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-5cadb2d00ec5426bb8ce252ae862143a
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

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