1,1,3,3-Tetramethylguanidine → 3-(3-Benzyloxyphenyl)-2-ethoxyacrylic acid ethyl ester

HRID 987119Notes

Reaction equation

HRID 987119 reaction equation
CN(C)C(=N)N(C)C.[CH2:9]([O:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH:20]=O)[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]>ClCCl>[CH2:33]([O:32][C:30](=[O:31])[C:29]([O:28][CH2:26][CH3:27])=[CH:20][C:19]1[CH:22]=[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]=1)[CH3:34]

Participants

5

Reactant 3

HCID 664601,1,3,3-TetramethylguanidineHCID 743423-BenzyloxybenzaldehydeHCID 11327835Phosphonium, (1,2-diethoxy-2-oxoethyl)triphenyl-, chloride (1:1)

Product 1

HCID 540313813-(3-Benzyloxyphenyl)-2-ethoxyacrylic acid ethyl esterYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tetramethylguanidine (6.5 g; 56.6 mmole) was slowly added to a solution of 3-benzyloxybenzaldehyde (11.7 g; 55 mmole) and (1,2-diethoxy-2-oxoethyl)(triphenyl) phosphonium chloride (20.1 g; 46.8 mmole) in dichloromethane (200 ml) at 0° C. After stirring at room temperature overnight the solvent was evaporated in vacuo. Diethyl ether was added and insoluble material was filtered off. The filtrate was washed with sodium bicarbonate solution, dried (magnesium sulfate), filtered and the solvent was evaporated in vacuo. The residue was purified by chromatography on silica gel using THY (0.5%) in dichloromethane as eluant. The remaining aldehyde was removed by stirring with sodium bisulfite in water and diethyl ether for 2 days. The phases were separated and the organic phase was evaporated in vacuo to give 10.5 g (yield 69%) of the desired product.

Workup

  1. customwas evaporated in vacuo
  2. additionDiethyl ether was added
  3. filtrationinsoluble material was filtered off
  4. washThe filtrate was washed with sodium bicarbonate solution
  5. dry with materialdried (magnesium sulfate)
  6. filtrationfiltered
  7. customthe solvent was evaporated in vacuo
  8. customThe residue was purified by chromatography on silica gel using THY (0.5%) in dichloromethane as eluant
  9. customThe remaining aldehyde was removed
  10. stirringby stirring with sodium bisulfite in water and diethyl ether for 2 days
  11. customThe phases were separated
  12. customthe organic phase was evaporated in vacuo

Sources & evidence

ORD record
ord-dd8559a077174b7d8b287ad94b0bc7c5
Source dataset
uspto-grants-2003_10
Patent number
US06630509B2

Reaction notes

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