L-Proline → HCID 53753559, compound

HRID 262222Notes

Reaction equation

HRID 262222 reaction equation
N1CCC[C@H:2]1[C:3](O)=[O:4].Br[CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][C:15]2[O:19][C:18]([N+:20]([O-:22])=[O:21])=[C:17]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:16]=2[CH:29]=1>C(O)C>[CH2:3]([O:4][CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][C:15]2[O:19][C:18]([N+:20]([O-:22])=[O:21])=[C:17]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:16]=2[CH:29]=1)[CH3:2]

Participants

4

Reactant 2

HCID 145742L-ProlineHCID 21320285HCID 21320285, compound

Product 1

HCID 53753559HCID 53753559, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1.04 g. (0.009 mole) of proline and 3 g. (0.009 mole) of 5-(2-bromoethyl)-2-nitro-3-phenylbenzofuran (prepared by reaction of 5-(2-hydroxyethyl)-2-nitro-3-phenylbenzofuran with phosphorus tribromide) in 50 ml. of ethanol is heated to its reflux temperature and maintained at reflux temperature for about 14 hours. The mixture is evaporated to provide a solid residue which is recrystallized from ethanol to provide 5-ethoxyethyl-2-nitro-3-phenylbenzofuran, m.p. 108°-109° C.

Workup

  1. additionA mixture of 1.04 g
  2. temperaturereflux temperature
  3. temperaturemaintained
  4. temperatureat reflux temperature for about 14 hours
  5. customThe mixture is evaporated
  6. customto provide a solid residue which
  7. customis recrystallized from ethanol

Sources & evidence

ORD record
ord-b5c233bafd7342148453bd61b190d816
Source dataset
uspto-grants-1979_05
Patent number
US04153716

Reaction notes

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