Tetrabutylammonium Fluoride Trihydrate → 1-Acetoxy-6-(10-acetoxydecyl)-2,3-dimethoxy-4-hydroxy-5-methylbenzene

HRID 1648701Notes

Reaction equation

HRID 1648701 reaction equation
[C:1]([O:4][C:5]1[C:10]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22](=[O:24])[CH3:23])=[C:9]([CH3:25])[C:8]([O:26][Si](C(C)(C)C)(C2C=CC=CC=2)C2C=CC=CC=2)=[C:7]([O:44][CH3:45])[C:6]=1[O:46][CH3:47])(=[O:3])[CH3:2].O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:1]([O:4][C:5]1[C:10]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22](=[O:24])[CH3:23])=[C:9]([CH3:25])[C:8]([OH:26])=[C:7]([O:44][CH3:45])[C:6]=1[O:46][CH3:47])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 194185161-Acetoxy-6-(10-acetoxydecyl)-4-tert-butyldiphenylsilyloxy-2,3-dimethoxy-5-methylbenzene

Product 1

HCID 194185331-Acetoxy-6-(10-acetoxydecyl)-2,3-dimethoxy-4-hydroxy-5-methylbenzeneYield 77.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Acetoxy-6-(10-acetoxydecyl)-4-tert-butyldiphenylsilyloxy-2,3-dimethoxy-5-methylbenzene (0.483 g) was dissolved in tetrahydrofuran (5 ml), and tetrabutylammonium fluoride trihydrate (0.5 g) was added. The mixture was stirred at room temperature for 30 minutes. After concentration under reduced pressure, the residue was subjected to column chromatography on silica gel and eluted with hexane/ethyl acetate (7:3) to obtain the desired compound (0.24 g).

Workup

  1. concentrationAfter concentration under reduced pressure
  2. washeluted with hexane/ethyl acetate (7:3)

Sources & evidence

ORD record
ord-385b6bed99d2470696b938c8d702da7d
Source dataset
uspto-grants-1995_07
Patent number
US05436359

Reaction notes

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