Tetrabutylammonium Fluoride → HCID 178450050, compound

HRID 480461Notes

Reaction equation

HRID 480461 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH3:19][CH:20]([CH3:66])[C:21]([C:47]1[CH:56]=[CH:55][C:54]2[C:49](=[CH:50][CH:51]=[C:52]([C:57]3[N:58]=[N:59][NH:60][C:61]=3[Si](C)(C)C)[CH:53]=2)[CH:48]=1)([C:23]1[N:24]=[CH:25][N:26](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:27]=1)[OH:22]>C1COCC1.O>[NH:26]1[CH:27]=[C:23]([C:21]([C:47]2[CH:56]=[CH:55][C:54]3[C:49](=[CH:50][CH:51]=[C:52]([C:57]4[N:58]=[N:59][NH:60][CH:61]=4)[CH:53]=3)[CH:48]=2)([OH:22])[CH:20]([CH3:19])[CH3:66])[N:24]=[CH:25]1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 178450053HCID 178450053, compound

Product 1

HCID 178450050HCID 178450050, compoundYield 166.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of tetrabutylammonium fluoride in THF (1M:3 mL) was added to a solution of 2-methyl-1-(6-(5-trimethylsilyl-1H-1,2,3-triazol-4-yl)-2-naphthyl)-1-(1-trityl-1H-imidazol-4-yl)-1-propanol (820 mg) in THF (3 mL) and the mixture was stirred at room temperature for 1 h. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried and concentrated. The residue was purified by column chromatography (eluent; hexane:THF=4:1) and crystallized from ethyl acetate-hexane to give the titled compound (703 mg) as a colorless powder.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (eluent; hexane:THF=4:1)
  6. customcrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-af9ac848571542edab67cf9bcd23762b
Source dataset
uspto-grants-2003_11
Patent number
US06649643B1

Reaction notes

Loading…