Water → 2-{[3-Methoxy-4-(2-thiophene-2-ylvinyl)phenyl]methylamino}ethanol

HRID 85311Notes

Reaction equation

[OH-].[Na+].O.[CH3:4][O:5][C:6]1[CH:7]=[C:8]([CH2:19][NH:20][CH2:21][CH2:22][O:23]C(=O)C(C)(C)C)[CH:9]=[CH:10][C:11]=1[CH:12]=[CH:13][C:14]1[S:15][CH:16]=[CH:17][CH:18]=1>C(O)C>[CH3:4][O:5][C:6]1[CH:7]=[C:8]([CH2:19][NH:20][CH2:21][CH2:22][OH:23])[CH:9]=[CH:10][C:11]=1[CH:12]=[CH:13][C:14]1[S:15][CH:16]=[CH:17][CH:18]=1

Participants

Conditions

Temperature: 45 °C

Procedure

NaOH (4.3 g, 107 mmol) was dissolved in ethanol (25 ml), and water (7 ml) was added thereto. Next, 2,2-dimethylpropionic acid 2-{[3-methoxy-4-(2-thiophene-2-ylvinyl)phenyl]methylamino}ethyl ester (4.0 g, 10.7 mmol) was dissolved in ethanol (8 ml) and added dropwise to the mixture. The mixture was stirred at room temperature for 2 hours and further at 45° C. for 1 hour. After the solvent was evaporated off, water (100 ml) was added and the oily matter was subjected to extraction with ethyl acetate. After 2 times of washing with water, drying over Na2SO4 and concentration were performed. The residue was purified by silica gel chromatography to give a yellow oily matter (yield: 3.1 g (100%)).

Workup

additionadded dropwise to the mixture
customAfter the solvent was evaporated off
additionwater (100 ml) was added
extractionthe oily matter was subjected to extraction with ethyl acetate
washAfter 2 times of washing with water
dry with materialdrying over Na2SO4 and concentration
customThe residue was purified by silica gel chromatography
customto give a yellow oily matter (yield: 3.1 g (100%))

Sources & evidence

ORD record: ord-46f212c4d6a142638df8ed39582b9f84
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846955B2

Reaction notes

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