TBAF tetrahydrofuran → HCID 20802592, compound

HRID 2420666Notes

Reaction equation

HRID 2420666 reaction equation
[Si]([O:8][C:9]1[C:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH3:22])=[CH:17][CH:16]=2)=[C:12]([C:23]([F:26])([F:25])[F:24])[N:11]([CH:27]([CH2:30][F:31])[CH2:28][F:29])[N:10]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>O1CCCC1>[CH2:21]([C:18]1[CH:17]=[CH:16][C:15]([CH2:14][C:13]2[C:9](=[O:8])[NH:10][N:11]([CH:27]([CH2:30][F:31])[CH2:28][F:29])[C:12]=2[C:23]([F:24])([F:25])[F:26])=[CH:20][CH:19]=1)[CH3:22]

Participants

4

Reactant 2

HCID 11078149TBAF tetrahydrofuranHCID 20802593HCID 20802593, compound

Product 1

HCID 20802592HCID 20802592, compoundYield 46.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

3-t-Butyldimethylsilyloxy-4-((4-ethylphenyl)methyl)-1-(1,3-difluoro-2-propyl)-5-(trifluoromethyl)pyrazole (1.95 g; 4.22 mmol) was dissolved in tetrahydrofuran (30 ml) and cooled to 0° C. A 1 M tetrabutylammonium fluoride-tetrahydrofuran solution (6.33 ml; 6.33 mmol) was gradually added, then the mixture was stirred at room temperature for 30 minutes. The reaction solution was concentrated, and the residue was purified on a silica gel column chromatography (ethyl acetate-hexane=1:4) to give the desired compound (684 mg; 1.96 mmol). (46%)

Workup

  1. concentrationThe reaction solution was concentrated
  2. customthe residue was purified on a silica gel column chromatography (ethyl acetate-hexane=1:4)

Sources & evidence

ORD record
ord-86318821cfa8460c812f956de5920d74
Source dataset
uspto-grants-2011_06
Patent number
US07956041B2

Reaction notes

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