Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → (E)-methyl 3-[3-(methylcarbamoyl)phenyl]prop-2-enoate

HRID 1092182Notes

Reaction equation

HRID 1092182 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([NH:8][CH3:9])=[O:7])=O.C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[CH:20][C:21]([O:23][CH3:24])=[O:22])C=CC=CC=1>ClCCl>[CH3:9][NH:8][C:6]([C:5]1[CH:4]=[C:3](/[CH:1]=[CH:20]/[C:21]([O:23][CH3:24])=[O:22])[CH:12]=[CH:11][CH:10]=1)=[O:7]

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 220514333-formyl-N-methylbenzamide

Product 1

HCID 66589796(E)-methyl 3-[3-(methylcarbamoyl)phenyl]prop-2-enoateYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-formyl-N-methylbenzamide (2.9 g, 17.77 mmol) and methyl 2-triphenylphosphoranylideneacetate (8.91 g, 26.66 mmol) in dichloromethane (85 mL), was stirred at room temperature for 18 h. The reaction mixture was evaporated to dryness. The crude product was purified by silica column chromatography, eluting with a gradient of 0 to 10% MeOH in DCM. Pure fractions were evaporated to dryness to afford impure product. Re-purified by silica column chromatography, eluting with a gradient of 50 to 100% EtOAc in hexanes. Pure fractions were evaporated to dryness to afford (E)-methyl 3-[3-(methylcarbamoyl)phenyl]prop-2-enoate (3.77 g, 97%).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. customThe crude product was purified by silica column chromatography
  3. washeluting with a gradient of 0 to 10% MeOH in DCM
  4. customPure fractions were evaporated to dryness
  5. customto afford impure product
  6. washRe-purified by silica column chromatography, eluting with a gradient of 50 to 100% EtOAc in hexanes
  7. customPure fractions were evaporated to dryness

Sources & evidence

ORD record
ord-ae3fad8ddc284bf79623f6ef6eee32f3
Source dataset
uspto-grants-2012_03
Patent number
US08129391B2

Reaction notes

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