Tetrabutylammonium Fluoride → HCID 15288847, compound

HRID 2399370Notes

Reaction equation

HRID 2399370 reaction equation
[Cl:1][C:2]1[CH:32]=[CH:31][C:5]2[O:6][C:7]3[CH:30]=[CH:29][CH:28]=[CH:27][C:8]=3[CH2:9][N:10]([C:11](=[O:26])/[CH:12]=[CH:13]/[CH2:14][C:15]([CH3:25])([O:20][Si](C)(C)C)[CH2:16][CH2:17][CH2:18][CH3:19])[C:4]=2[CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>>[Cl:1][C:2]1[CH:32]=[CH:31][C:5]2[O:6][C:7]3[CH:30]=[CH:29][CH:28]=[CH:27][C:8]=3[CH2:9][N:10]([C:11](=[O:26])/[CH:12]=[CH:13]/[CH2:14][C:15]([OH:20])([CH3:25])[CH2:16][CH2:17][CH2:18][CH3:19])[C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 15288846HCID 15288846, compound

Product 1

HCID 15288847HCID 15288847, compoundYield 3%

Procedure

To a stirring solution of 5 (2.0 g), was added tetrabutyl ammonium fluoride (22 mL, 22 mmol in THF). The crude product was used due to the difficulty of separating compounds 1 and 5. The reaction mixture was stirred for 45 minutes at room temperature. The solvent was removed under reduced pressure and the residue was taken up in CHCl3, extracted with brine and dried (K2CO3). The product was purified by MPLC (silica gel, 3:7 EtOAc:hexane) to yield 6 as a yellow oil (50 mg). Analysis calculated for C23H26ClNO3 : C: 69.08; H: 6.55; N: 3.50. Found C: 69.33; H: 6.64; N: 3.45.

Workup

  1. customThe solvent was removed under reduced pressure
  2. extractionextracted with brine
  3. dry with materialdried (K2CO3)
  4. customThe product was purified by MPLC (silica gel, 3:7 EtOAc:hexane)

Sources & evidence

ORD record
ord-3274cac3b20148aab273653b782311fe
Source dataset
uspto-grants-1995_09
Patent number
US05449673

Reaction notes

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