Tetrabutylammonium Fluoride → HCID 136344866, compound

HRID 573192Notes

Reaction equation

HRID 573192 reaction equation
[Si]([O:8][C:9]1[CH:17]=[C:16]([F:18])[CH:15]=[C:14]2[C:10]=1[CH:11]=[N:12][N:13]2[CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[F:18][C:16]1[CH:17]=[C:9]([OH:8])[C:10]2[CH:11]=[N:12][N:13]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:25])([CH3:24])[CH3:26])[C:14]=2[CH:15]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67227952HCID 67227952, compound

Product 1

HCID 136344866HCID 136344866, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of EXAMPLE 414B (1.8 g) and 1.0 N tetrabutyl ammonium fluoride (13.6 mL) in tetrahydrofuran (15 mL) was stirred for 2 hours. The solvent was removed, and the residue was partitioned between water and ethyl acetate. The organic layer was separated, and the aqueous layer was extracted with additional ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified by flash chromatography on silica gel to give the title compound.

Workup

  1. customThe solvent was removed
  2. customthe residue was partitioned between water and ethyl acetate
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with additional ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-8cc35c7bebff44cf8d2734c7cf2e1c74
Source dataset
uspto-grants-2015_05
Patent number
US09029404B2

Reaction notes

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