Ethanolamine → 1-(2-Hydroxyethylamino)-3-[11-(butyldimethylsilyl)undecyloxy]-2-propanol

HRID 1101

Reaction equation

[CH2:1]([CH2:3][NH2:4])[OH:2].N#N.[CH2:7]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][Si:23]([CH2:26][CH2:27][CH2:28][CH3:29])([CH3:25])[CH3:24])[CH:8]1[O:10][CH2:9]1>C(O)C>[OH:2][CH2:1][CH2:3][NH:4][CH2:9][CH:8]([OH:10])[CH2:7][O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][Si:23]([CH2:26][CH2:27][CH2:28][CH3:29])([CH3:25])[CH3:24]

Participants

Conditions

Temperature: 80 °C

Procedure

A 100-ml two-necked flask equipped with a stirrer, dropping funnel and N2 inlet tube was charged with 4.58 g (75 mmol) of ethanolamine and 9.2 g of ethanol. The contents were heated to 80° C. with stirring in an N2 atmosphere, and an ethanol solution of 1.71 g (5 mmol) of 11-(butyldimethylsilyl)undecyl glycidyl ether was added dropwise to the contents over 1 hour. The resultant mixture was stirred further for 1 hour at 80° C. After completion of the reaction, ethanol and excess ethanolamine were distilled off under reduced pressure, and the resultant residue was purified by column chromatography on silica gel, thereby obtaining 1.48 g (yield: 73%) of the title compound (Ia-18).

Workup

customA 100-ml two-necked flask equipped with a stirrer
distillationwere distilled off under reduced pressure
customthe resultant residue was purified by column chromatography on silica gel

Sources & evidence

ORD record: ord-2859afa0baa6419ab73c46a66ac9120c
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05723497

Linked notes

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