Tetrabutylammonium Fluoride → HCID 66774882, compound

HRID 1644410Notes

Reaction equation

HRID 1644410 reaction equation
[Si]([O:8][CH2:9][CH2:10][N:11]1[C:16]2[CH:17]=[C:18]([O:21][CH3:22])[CH:19]=[CH:20][C:15]=2[O:14][CH2:13][C:12]1=[O:23])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[OH:8][CH2:9][CH2:10][N:11]1[C:16]2[CH:17]=[C:18]([O:21][CH3:22])[CH:19]=[CH:20][C:15]=2[O:14][CH2:13][C:12]1=[O:23]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 66774191HCID 66774191, compound2×

Product 1

HCID 66774882HCID 66774882, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-6-methoxy-2H-1,4-benzoxazin-3(4H)-one (Intermediate 127, 1.38 g, 4.1 mmol) in tetrahydrofuran (40 mL) was added tetrabutyl ammonium fluoride (1M in tetrahydrofuran (THF), 4.1 mL, 4.1 mmol). The reaction was stirred at room temperature for two hours. The solvent was removed under reduced pressure and the residue was taken up in dichloromethane, washed with water and dried over magnesium sulfate. Chromatography on silica gel using dichloromethane/methanol (95:5) gave the title compound as a yellow oil (570 mg, 62%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-15b221f530d14ab8957468c03978e531
Source dataset
uspto-grants-2012_02
Patent number
US08124602B2

Reaction notes

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