Tetrabutylammonium Fluoride → HCID 178482578, compound

HRID 25340Notes

Reaction equation

HRID 25340 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH3:19][N:20]([CH3:46])[CH:21]1[C:30]2[CH2:29][O:28][C:27]([CH:31]=[O:32])=[CH:26][C:25]3=[CH:33][N:34]([Si](C(C)C)(C(C)C)C(C)C)[CH:35]=[C:23]([C:24]=23)[CH2:22]1>O1CCCC1.O.C(OCC)(=O)C>[CH3:19][N:20]([CH3:46])[CH:21]1[C:30]2[CH2:29][O:28][C:27]([CH:31]=[O:32])=[CH:26][C:25]3=[CH:33][NH:34][CH:35]=[C:23]([C:24]=23)[CH2:22]1

Participants

6

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 865905898-Dimethylamino-2-triisopropylsilanyl-2,7,8,9-tetrahydro-6-oxa-2-azabenzo[cd]-azulene-5-carbaldehyde

Product 1

HCID 178482578HCID 178482578, compoundYield 88%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Tetra-n-butylammoniumfluoride (1 mol/l tetrahydrofuran solution) 2.2 ml was added to compound (45) 496 mg in tetrahydrofuran 10 ml with cooling in ice. The mixture was stirred for 3 h, diluted with water and ethyl acetate and, extracted with ethyl acetate. The extracts were washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue obtained was chromatographed on aluminum oxide in ethyl acetate:hexane (2:1) to give colorless crystals, 273.2 mg. This was recrystallized from acetone-isopropyl ether to give the titled compound as colorless crystals, m.p.175-176° C., 2654 mg. Yield 88%.

Workup

  1. temperaturewith cooling in ice
  2. extractionextracted with ethyl acetate
  3. washThe extracts were washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue obtained
  7. customwas chromatographed on aluminum oxide in ethyl acetate:hexane (2:1)
  8. customto give colorless crystals, 273.2 mg
  9. customThis was recrystallized from acetone-isopropyl ether

Sources & evidence

ORD record
ord-fd11c019ffe54a1ebbfe930daf4acdee
Source dataset
uspto-grants-2005_02
Patent number
US06858640B2

Reaction notes

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