Formaldehyde → HCID 67376231, compound

HRID 490922Notes

Reaction equation

HRID 490922 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])=[CH:8][CH:7]=1)[CH3:2].C=O.[C:26](=O)([O-])[O-].[K+].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:23])[C:5]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:14])=[CH:8][CH:7]=1)=[CH2:26])[CH3:2]

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 67375141HCID 67375141, compound

Product 1

HCID 67376231HCID 67376231, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 1140TolueneSolvent

Procedure

A solution of 2-(4-(benzyloxycarbonylamino)phenyl)ethanoic acid ethyl ester (6.5 g, 23.3 mmol), paraformaldehyde (1.05 g), potassium carbonate (5.15 g, 37.3 mmol) and tetrabutylammonium iodide (0.172 g, 0.5 mmol) in 230 mL of toluene was heated at 100° C. for 4 hours with stirring. The reaction mixture was filtered and the filtrate was washed with water, 1 M sodium hydrogen sulfate, and brine. The organic layer was evaporated in vacuo to afford 5.2 g of crude product. The product was purified by flash chromatography through silica gel (5/1 hexanes/ethyl acetate) to afford 2-(4-(benzyloxycarbonylamino)phenyl)prop-2-enoic acid ethyl ester 3.04 g (45%) as a white solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe filtrate was washed with water, 1 M sodium hydrogen sulfate, and brine
  3. customThe organic layer was evaporated in vacuo
  4. customto afford 5.2 g of crude product
  5. customThe product was purified by flash chromatography through silica gel (5/1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-a922e096d9414b15b4de7dc1f68aeb5f
Source dataset
uspto-grants-2009_05
Patent number
US07528173B2

Reaction notes

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