Water → HCID 19797745, compound

HRID 5049Notes

Reaction equation

[Cl-].[NH4+].O.C(O)(C)C.[C:8]([O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([N+:29]([O-])=O)[CH:24]=1)(=[O:12])[C:9]([CH3:11])=[CH2:10]>C(OCC)(=O)C>[C:8]([O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([NH2:29])[CH:24]=1)(=[O:12])[C:9]([CH3:11])=[CH2:10]

Participants

Conditions

Temperature: 75 °C

Procedure

A mixture of 25 g of reduced iron, 1 g of ammonium chloride, 50 ml of water, and 250 ml of isopropyl alcohol was raised to a temperature of 75° C. with stirring and after adding dropwise an ethyl acetate solution of the compound (1-B) to the aqueous solution (the mixture) over a period of one hour, the resultant mixture was further stirred for 2 hours. After removing insoluble matters from the reaction mixture by filtration, 200 ml of ethyl acetate and 500 ml of water were added to the reaction mixture and the ethyl acetate layer was extracted. The ethyl acetate layer was concentrated and the residue was purified by silica gel column chromatography using chloroform as a developing solvent to provide 15.3 g of 2-(2-(2-(3-aminophenoxy)ethoxy)ethoxy)ethyl methacrylate (1-C).

Workup

customAfter removing insoluble matters from the reaction mixture
filtrationby filtration, 200 ml of ethyl acetate and 500 ml of water
additionwere added to the reaction mixture
extractionthe ethyl acetate layer was extracted
concentrationThe ethyl acetate layer was concentrated
customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-3c1df7ab18894dd9a67c2c7d77a2304e
Source dataset: uspto-grants-1993_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05243004

Reaction notes

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