O-Xylene → HCID 14229720, compound

HRID 1761919Notes

Reaction equation

HRID 1761919 reaction equation
[C:1]1([C:7]2[O:8][C:9]3[C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=[CH:12][C:10]=3[CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:20]1([CH2:26]CO)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.C1(C)C(C)=CC=CC=1.[OH-].[Na+]>CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4].C1(C)C=CC=CC=1>[C:1]1([C:7]2[O:8][C:9]3[C:15]([C:16]([O:18][CH2:19][CH2:26][N:20]4[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]4)=[O:17])=[CH:14][CH:13]=[CH:12][C:10]=3[CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 7237O-XyleneHCID 14798Sodium HydroxideHCID 18232N-PiperidinoethanolHCID 14229719HCID 14229719, compound

Product 1

HCID 14229720HCID 14229720, compoundYield 95.9%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 0.76 g of methyl 2-phenylbenzofuran-7-carboxylate, 0.46 g of 2-piperidinoethanol, 0.05 g of tetraisopropyl orthotitanate and 5 ml of xylene is refluxed for 4 hours. Toluene and an aqueous 10% sodium hydroxide solution are added to the reaction mixture and the mixture is filtered. The filtrate is washed with water, dried and evaporated to remove solvent. The residue is purified by silica gel column chromatography (solvent; chloroform:methanol=10:1) to give 1.01 g of 2-piperidinoethyl 2-phenylbenzofuran-7-carboxylate as pale yellow oil.

Workup

  1. temperatureis refluxed for 4 hours
  2. filtrationthe mixture is filtered
  3. washThe filtrate is washed with water
  4. customdried
  5. customevaporated
  6. customto remove solvent
  7. customThe residue is purified by silica gel column chromatography (solvent; chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-a48831b10d55449e82a3187128b59908
Source dataset
uspto-grants-1989_05
Patent number
US04829067

Reaction notes

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