Acetic Acid → 1-(4-bromophenyl)-4-(2,2-dimethyl-3-tetrahydro-2H-pyrane-2-yloxypropionyl)-3-hydroxy-5-(2-methoxyphenyl)-1,5-dihydropyrrole-2-one

HRID 2037182Notes

Reaction equation

HRID 2037182 reaction equation
[CH3:1][C:2]([CH3:20])([CH2:12][O:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][O:15]1)[C:3](=[O:11])[CH2:4][C:5](=[O:10])[C:6]([O:8]C)=O.[Br:21][C:22]1[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][CH:23]=1.[CH3:29][O:30][C:31]1[CH:38]=[CH:37][CH:36]=[CH:35][C:32]=1[CH:33]=O.C(O)(=O)C>O1CCOCC1>[Br:21][C:22]1[CH:28]=[CH:27][C:25]([N:26]2[CH:33]([C:32]3[CH:35]=[CH:36][CH:37]=[CH:38][C:31]=3[O:30][CH3:29])[C:4]([C:3](=[O:11])[C:2]([CH3:1])([CH3:20])[CH2:12][O:13][CH:14]3[CH2:19][CH2:18][CH2:17][CH2:16][O:15]3)=[C:5]([OH:10])[C:6]2=[O:8])=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 78074-BromoanilineHCID 86582-MethoxybenzaldehydeHCID 58365520methyl 5,5-dimethyl-2,4-dioxo-6-(tetrahydro-2H-pyrane-2-yloxy)hexanoate

Product 1

HCID 583654321-(4-bromophenyl)-4-(2,2-dimethyl-3-tetrahydro-2H-pyrane-2-yloxypropionyl)-3-hydroxy-5-(2-methoxyphenyl)-1,5-dihydropyrrole-2-oneYield 33%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of methyl 5,5-dimethyl-2,4-dioxo-6-(tetrahydro-2H-pyrane-2-yloxy)hexanoate (4.29 g, 15 mmol), 4-bromoaniline (2.58 g, 15 mmol), 2-methoxybenzaldehyde (1.812 mL, 15 mmol), acetic acid (0.343 mL, 6 mmol) and dioxane (15 ml) was heated at reflux overnight. After the reaction was completed, the mixture was concentrated in vacuo and the resulting residue was purified on a silica gel column chromatography (ethyl acetate/n-hexane). The resulting aimed compound was triturated with ethyl acetate and n-hexane to give 1-(4-bromophenyl)-4-(2,2-dimethyl-3-tetrahydro-2H-pyrane-2-yloxypropionyl)-3-hydroxy-5-(2-methoxyphenyl)-1,5-dihydropyrrole-2-one (2.69 g, yield: 33%) as colorless solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. concentrationthe mixture was concentrated in vacuo
  4. customthe resulting residue was purified on a silica gel column chromatography (ethyl acetate/n-hexane)
  5. customThe resulting aimed compound was triturated with ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-5b2f6290f21047d2b0670a60faf6c469
Source dataset
uspto-grants-2013_11
Patent number
US08575197B2

Reaction notes

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