Tetrabutylammonium Fluoride → HCID 136344871, compound

HRID 2045104Notes

Reaction equation

HRID 2045104 reaction equation
[Si]([O:8][C:9]1[C:17]2[N:16]=[N:15][N:14]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[C:13]=2[CH:12]=[CH:11][CH:10]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH3:23][Si:22]([CH3:25])([CH3:24])[CH2:21][CH2:20][O:19][CH2:18][N:14]1[C:13]2[CH:12]=[CH:11][CH:10]=[C:9]([OH:8])[C:17]=2[N:16]=[N:15]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67226747HCID 67226747, compound

Product 1

HCID 136344871HCID 136344871, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of EXAMPLE 514B (1.32 g) and 1.0 N tetrabutyl ammonium fluoride (10.4 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 using 10% ethyl acetate in hexanes as eluent 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 using 10% ethyl acetate in hexanes as eluent

Sources & evidence

ORD record
ord-0455b3eee2f94060afe64f657f52b8f9
Source dataset
uspto-grants-2013_11
Patent number
US08586754B2

Reaction notes

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