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

HRID 1734940Notes

Reaction equation

HRID 1734940 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-ae55b3550fca4d0d864ae242bc61382c
Source dataset
uspto-grants-1996_07
Patent number
US05534639

Reaction notes

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