Tetrabutylammonium Fluoride → HCID 66670086, compound

HRID 1014926Notes

Reaction equation

HRID 1014926 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH:14]([O:16]C(=O)C)[CH2:13][CH:12]1[CH2:20][C:21]1[C:29]2[C:24](=[N:25][CH:26]=[CH:27][CH:28]=2)[N:23]([C:30](=[O:32])[CH3:31])[CH:22]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH:14]([OH:16])[CH2:13][CH:12]1[CH2:20][C:21]1[C:29]2[C:24](=[N:25][CH:26]=[CH:27][CH:28]=2)[N:23]([C:30](=[O:32])[CH3:31])[CH:22]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 66670107HCID 66670107, compound

Product 1

HCID 66670086HCID 66670086, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution containing 70 (2.99 g, 5.88 mmol) in THF (20 ml) at 0° C. was added a solution of TBAF (1M in THF, 11.8 mL, 11.8 mmol) in a dropwise fashion. After 1.5 h, TLC analysis revealed complete consumption of 70 [1:1 hexanes EtOAc, Rf(70)=0.64; Rf(71)=0.3]. The solvent was removed in vacuo and the residue was dissolved in EtOAc and washed with water, brine, dried over anhydrous Na2SO4, filtered, and concentrated to afford 2.11 g of crude 71 which was used without further purification.

Workup

  1. customconsumption of 70 [1:1 hexanes EtOAc, Rf(70)=0.64; Rf(71)=0.3]
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in EtOAc
  4. washwashed with water, brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford 2.11 g of crude 71 which
  9. customwas used without further purification

Sources & evidence

ORD record
ord-0b2118e9ae1a426f9d2b4f259a35d69d
Source dataset
uspto-grants-2011_07
Patent number
US07985735B2

Reaction notes

Loading…