Cesium carbonate → HCID 53814537, compound

HRID 1684756Notes

Reaction equation

HRID 1684756 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:5]=1[O:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][CH3:17].Cl[CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)=[CH:6][C:5]=1[O:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][CH3:17]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 767274-(2-Chloroethyl)morpholineHCID 53804555HCID 53804555, compound

Product 1

HCID 53814537HCID 53814537, compoundYield 102.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of 4-hydroxy-2-(4-methoxybutoxy)-benzoic acid methyl ester (2.0 g), 2-chloroethylmorpholine (11.8 g) and caesium carbonate (12.8 g) in acetone (30 ml) is stirred under reflux for 2 hours. Filtration and purification by FC (80 g of silica gel, eluant F and ethyl acetate-conc. ammonia 10:0.1) yield 2-(4-methoxy butoxy)-4-(2-morpholin-4-ylethoxy)-benzoic acid methyl ester (2.96 g), Rf (N)=0.73, in the form of a pale-yellow oil.

Workup

  1. temperatureunder reflux for 2 hours
  2. filtrationFiltration and purification by FC (80 g of silica gel, eluant F and ethyl acetate-conc. ammonia 10:0.1)

Sources & evidence

ORD record
ord-634d333c01dc4af1899a60ba5d610150
Source dataset
uspto-grants-1997_06
Patent number
US05641778

Reaction notes

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