Formaldehyde → HCID 67376231, compound

HRID 1677598Notes

Reaction equation

HRID 1677598 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-55c6815e406d494fa62006eba3df088d
Source dataset
uspto-grants-2011_08
Patent number
US08008325B2

Reaction notes

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