Tetrabutylammonium Fluoride → HCID 69793566, compound

HRID 495605Notes

Reaction equation

HRID 495605 reaction equation
[Si]([O:8][CH2:9][C@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[CH:16]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH3:21][C:17]1[CH:16]=[C:15]([N:11]2[CH2:12][CH2:13][CH2:14][C@@H:10]2[CH2:9][OH:8])[CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 69794047HCID 69794047, compound

Product 1

HCID 69793566HCID 69793566, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of D4 (7.20 g, 0.024 mol) in THF (50 ml) was treated with tetrabutylammonium fluoride (1M solution in THF, 2 eq., 96 ml) and then stirred at ambient temperature for 18 h. Solvent was removed under reduced pressure and residue chromatographed on silica gel eluting with EtOAc in hexane (gradient elution, maximum 50%) to afford the product as an oil (3.70 g, 81%).

Workup

  1. customSolvent was removed under reduced pressure and residue
  2. customchromatographed on silica gel eluting with EtOAc in hexane (gradient elution, maximum 50%)

Sources & evidence

ORD record
ord-0c86e3b0e75b42069eb27f2eb9133e4e
Source dataset
uspto-grants-2005_09
Patent number
US06939891B2

Reaction notes

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