Tetrabutylammonium Fluoride → 2-[5-(6-Chloro-2-methylpyridin-3-yl)-1,2,4-oxadiazol-3-yl]ethanol

HRID 385963Notes

Reaction equation

HRID 385963 reaction equation
[Si]([O:18][CH2:19][CH2:20][C:21]1[N:25]=[C:24]([C:26]2[C:27]([CH3:33])=[N:28][C:29]([Cl:32])=[CH:30][CH:31]=2)[O:23][N:22]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[Cl:32][C:29]1[N:28]=[C:27]([CH3:33])[C:26]([C:24]2[O:23][N:22]=[C:21]([CH2:20][CH2:19][OH:18])[N:25]=2)=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 595256053-[3-(2-{[tert-Butyl(diphenyl)silyl]oxy}ethyl)-1,2,4-oxadiazol-5-yl]-6-chloro-2-methylpyridine

Product 1

HCID 595258502-[5-(6-Chloro-2-methylpyridin-3-yl)-1,2,4-oxadiazol-3-yl]ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

3-[3-(2-{[tert-Butyl(diphenyl)silyl]oxy}ethyl)-1,2,4-oxadiazol-5-yl]-6-chloro-2-methylpyridine (210 mg, 0.44 mmol) was taken up in tetrahydrofuran (2.2 ml) and tetrabutylammonium fluoride (0.44 ml of 1.0 M in THF, 0.44 mmol) was added. The solution was heated to 50° C. for 2 hours, cooled to room temperature, concentrated under reduced pressure, and directly purified via silica gel chromatography (0-100% ethyl acetate in hexane) to afford the title compound.

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. customdirectly purified via silica gel chromatography (0-100% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-25a6fe6f4beb40d88a9b5250aee69186
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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