Tetrabutylammonium Fluoride → HCID 86619476, compound

HRID 254814Notes

Reaction equation

HRID 254814 reaction equation
[C:1]([C:5]1[O:6][C:7]([C:10]2[C:14]([CH2:15][C:16]#[C:17][Si](C)(C)C)=[C:13]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)[N:12]([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][C:30]=3[Cl:36])[N:11]=2)=[N:8][N:9]=1)([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.CCOCC.O>[C:1]([C:5]1[O:6][C:7]([C:10]2[C:14]([CH:15]=[C:16]=[CH2:17])=[C:13]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)[N:12]([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][C:30]=3[Cl:36])[N:11]=2)=[N:8][N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 66844713HCID 66844713, compound

Product 1

HCID 86619476HCID 86619476, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-tert-butyl-5-(5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-(3-(trimethylsilyl)prop-2-ynyl)-1H-pyrazol-3-yl)-1,3,4-oxadiazole (300 mg, 0.46 mmol) in tetrahydrofuran (5 ml) at 0° C. was added tetrabutylammonium fluoride (0.7 ml, 1.0 M in tetrahydrofuran, 0.7 mmol). After reaction mixture was warmed up to room temperature, it was stirred for 10 minutes. After the resulting solution was diluted with ether (20 ml), water was added (10 ml). Organic layer was separated with ethyl acetate (20 ml twice). After evaporation, crude residue was purified with silica gel column (hexane/ethyl acetate=7/1 to hexane/ethyl acetate 5/1). The less polar compound 2-tert-butyl-5-(5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-(propa-1,2-dienyl)-1H-pyrazol-3-yl)-1,3,4-oxadiazole was obtained as light yellow solid (87 mg, 34% yield). And relatively more polar compound 2-tert-butyl-5-(5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-(prop-2-ynyl)-1H-pyrazol-3-yl)-1,3,4-oxadiazole was produced as yellow solid (140 mg, 54% yield).

Workup

  1. customAfter reaction mixture
  2. additionwas added (10 ml)
  3. customOrganic layer was separated with ethyl acetate (20 ml twice)
  4. customAfter evaporation, crude residue
  5. customwas purified with silica gel column (hexane/ethyl acetate=7/1 to hexane/ethyl acetate 5/1)

Sources & evidence

ORD record
ord-28637859a8254c4280c17802b5f03363
Source dataset
uspto-grants-2011_01
Patent number
US07875647B2

Reaction notes

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