Diethylethanolamine → (+/-)-2-Diethylaminoethyl 2-(2-naphthylmethoxy)-3,3,3-trifluoro-2-methylpropionate
Reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]([CH3:21])([C:17]([F:20])([F:19])[F:18])[C:14](Cl)=[O:15].[CH2:22]([N:24]([CH2:28][CH3:29])[CH2:25][CH2:26][OH:27])[CH3:23]>CCOCC>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]([CH3:21])([C:17]([F:20])([F:19])[F:18])[C:14]([O:27][CH2:26][CH2:25][N:24]([CH2:28][CH3:29])[CH2:22][CH3:23])=[O:15]Participants
Procedure
A solution of (±)-2-(2-naphthylmethoxy)-3,3,3-trifluoro-2-methylpropionyl chloride (3.0 g.) in ether (20 ml.) is added dropwise at ambient temperature to a stirred solution of 2-diethylaminoethanol (3.0 ml.) in ether (100 ml.). The mixture is stored for 18 hours, filtered, and the solid is washed with ether. The filtrate and washings are evaporated to an oil (3.5 g.), which is dissolved in ether and run through a column of silica gel made up in ether. The column is eluted with 200 ml. of ether, and the eluate evaporated to give 2.4 g. of an oil which is similarly passed through a column of alumina (Neutral, Grade I, 30 g.). Elution with ether yields (±)-2-diethylaminoethyl 2-(2-naphthylmethoxy)-3,3,3-trifluoro-2-methylpropionate (1.05 g.) as an oil.
Workup
- filtrationfiltered
- washthe solid is washed with ether
- customThe filtrate and washings are evaporated to an oil (3.5 g.), which
- dissolutionis dissolved in ether
- washThe column is eluted with 200 ml
- customof ether, and the eluate evaporated
- customto give 2.4 g
- washElution with ether
Sources & evidence
- ORD record
- ord-6c3838f9cf3c4696a2011a90690d25ae
- Source dataset
- uspto-grants-1978_08
- Patent number
- US04107329
Reaction notes
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