Tetrabutylammonium Fluoride → HCID 22042620, compound

HRID 1791015Notes

Reaction equation

HRID 1791015 reaction equation
[OH:1][C:2]([C:13]1[CH:18]=[CH:17][C:16]([N:19]([CH2:29][CH:30]([CH3:32])[CH3:31])[S:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)(=[O:22])=[O:21])=[CH:15][CH:14]=1)([C:9]([F:12])([F:11])[F:10])[C:3]#[C:4][Si](C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C(Cl)Cl.C1COCC1>[OH:1][C:2]([C:13]1[CH:18]=[CH:17][C:16]([N:19]([CH2:29][CH:30]([CH3:32])[CH3:31])[S:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)(=[O:22])=[O:21])=[CH:15][CH:14]=1)([C:9]([F:12])([F:11])[F:10])[C:3]#[CH:4]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 22042578HCID 22042578, compound

Product 1

HCID 22042620HCID 22042620, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.25 g (0.51 mmol) of N-[4-(1-hydroxy-1-trifluoromethyl-3-trimethylsilanyl-prop-2-ynyl)-phenyl]-N-isobutyl-benzenesulfonamide (Example 74) in 6 mL of CH2Cl2 was added 0.4 mL of a 1 M solution of tetrabutylammonium fluoride in THF. The mixture was stirred at room temperature for 1 hour. CH2Cl2 (60 mL) was added and the solution was washed with saturated aqueous NH4Cl-solution (20 mL) and brine (15 mL). The organic layer was dried over Na2SO4, filtered and the filtrate was concentrated. The residue was purified by chromatography on silica gel, (hexane:EtOAc, 7:3) to give the title compound.

Workup

  1. washthe solution was washed with saturated aqueous NH4Cl-solution (20 mL) and brine (15 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by chromatography on silica gel, (hexane:EtOAc, 7:3)

Sources & evidence

ORD record
ord-68c1b2678fec4a839319799f6101cb08
Source dataset
uspto-grants-2006_07
Patent number
US07071358B2

Reaction notes

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