Hydroxide → HCID 86750312, compound

HRID 1450249Notes

Reaction equation

HRID 1450249 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][C:18]=1[N+:19]([O-:21])=[O:20])[O:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=O.[OH:22][C:23]1[NH:24][C:25](=[O:47])[CH2:26][C:27]=1[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[OH-]>C(O)C>[O:22]=[C:23]1[NH:24][C:25](=[O:47])[CH2:26]/[C:27]/1=[CH:1]\[C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][C:18]=1[N+:19]([O-:21])=[O:20])[O:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

5

Reactant 3

HCID 961HydroxideHCID 10979330Pentanoic acid, 5-(3-formyl-4-nitrophenoxy)-, ethyl esterHCID 19975655HCID 19975655, compound

Product 1

HCID 86750312HCID 86750312, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 5-(3-formyl-4-nitrophenoxy)pentanoate (0.60 mol) and (4,5-di-hydro-2-hydroxy-5-oxo-1H-pyrrol-3-yl)triphenylphosphonium, hydroxide, inner salt (0.57 mol) in ethanol (1500 ml) was stirred and refluxed for 1 hour. The solvent was removed. The residue was stirred in methylbenzene. The resulting precipitate was filtered off, washed with methylbenzene, 2,2'-oxybispropane and dried, yielding 137.3 g (61%) of (E)-ethyl 5-[3-[(2,5-dioxo-3-pyrrolidinylidene)methyl]-4-nitrophenoxy]pentanoate; mp. 112.4° C. (interm. 1).

Workup

  1. temperaturerefluxed for 1 hour
  2. customThe solvent was removed
  3. stirringThe residue was stirred in methylbenzene
  4. filtrationThe resulting precipitate was filtered off
  5. washwashed with methylbenzene, 2,2'-oxybispropane
  6. customdried

Sources & evidence

ORD record
ord-40f8c117d748466aa91f9571e2197323
Source dataset
uspto-grants-1997_02
Patent number
US05602134

Reaction notes

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