tert-Butanol → 1-(6-(2,2,2-Trifluoroethoxy)pyridin-3-yl)ethane-1,2-diol
Reaction equation
[C:1]([OH:5])(C)([CH3:3])[CH3:2].CC[C@@H]1[C@@H]2C[C@H]([C@@H](OC3C4C(=CC=CC=4)C(O[C@@H](C4C=CN=C5C=4C=C(OC)C=C5)[C@@H]4N5C[C@H](CC)[C@@H](CC5)C4)=NN=3)C3C=CN=C4C=3C=C([O:27]C)C=C4)N(CC2)C1.[F:64][C:65]([F:77])([F:76])[CH2:66][O:67][C:68]1[CH:73]=[CH:72]C(C=C)=[CH:70][N:69]=1>O>[F:64][C:65]([F:77])([F:76])[CH2:66][O:67][C:68]1[N:69]=[CH:70][C:2]([CH:1]([OH:5])[CH2:3][OH:27])=[CH:72][CH:73]=1Participants
Procedure
A 200 mL flask is charged with tert-butanol (30 mL), water (30 mL) and AD-mix-beta (10 g, 4.92 mmol). Stirring room temperature producted two clear phased. The lower aquerous phase bright yellow. The mixture is cooled to 0° C. Whereupon some of the dissolved salts precipitate. 2-(2,2,2-trifluoroethoxy)-5-vinylpyridine (1.00 g, 4.92 mmol, Step-2) is added at once, and the heterogeneous slurry is stirred vigorously at 0° C. for 15 hours. White precipitate is filtrated and filtrate is removed under reduced pressure. The residue is extracted with ethyl acetate and dried over sodium sulfate and concentrated in vacuo. The residue is purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (1:3) to give 1.01 g (86% yield) of the title compound as colorless oil.
Workup
- temperatureThe mixture is cooled to 0° C
- stirringis stirred vigorously at 0° C. for 15 hours
- filtrationWhite precipitate is filtrated
- customfiltrate is removed under reduced pressure
- extractionThe residue is extracted with ethyl acetate
- dry with materialdried over sodium sulfate
- concentrationconcentrated in vacuo
- customThe residue is purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (1:3)
Sources & evidence
- ORD record
- ord-2abfa2837b004f299251ad775594e269
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09302991B2
Reaction notes
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