Tetrabutylammonium Fluoride → HCID 66774882, compound

HRID 255289Notes

Reaction equation

HRID 255289 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-b50635f776d242c49b964541937146dd
Source dataset
uspto-grants-2011_01
Patent number
US07875715B2

Reaction notes

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