Ethanolamine → Butyl 12-[2-hydroxy-3-(2-hydroxyethylamino)propoxy]dodecanate

HRID 1099

Reaction equation

[CH2:1]([CH2:3][NH2:4])[OH:2].C(O)C.[O:8]1[CH2:30][CH:9]1[CH2:10][O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][CH2:27][CH2:28][CH3:29])=[O:24]>O>[OH:8][CH:9]([CH2:30][NH:4][CH2:3][CH2:1][OH:2])[CH2:10][O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][CH2:27][CH2:28][CH3:29])=[O:24]

Participants

Conditions

Temperature: 80 °C

Procedure

A 100-ml flask equipped with a stirrer and dropping funnel was charged with 23.7 g (250 mmol) of ethanolamine and 23.7 g of ethanol. While stirring the mixture at 80° C., an ethanol solution of 8.20 g (25 mmol) of butyl 12-(2,3-epoxypropoxy)-dodecanate was added dropwise over 1 hour. After completion of the reaction, water was added to the reaction mixture, followed by extraction with chloroform. The resultant chloroform solution was concentrated under reduced pressure, and the resultant residue was purified by column chromatography on silica gel, thereby obtaining 5.40 g (yield: 55.4%) of the title compound (Ia-15).

Workup

customA 100-ml flask equipped with a stirrer
additionwas added to the reaction mixture
extractionfollowed by extraction with chloroform
concentrationThe resultant chloroform solution was concentrated under reduced pressure
customthe resultant residue was purified by column chromatography on silica gel

Sources & evidence

ORD record: ord-47ed777a87bd4c2eaf51117084ffdcc4
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05723497

Linked notes

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