Tert-butyl-(3,5-diethoxy-4-fluoro-benzyloxy)-dimethyl-silane → (3,5-Diethoxy-4-fluorophenyl)methanol

HRID 2355582Notes

Reaction equation

HRID 2355582 reaction equation
C([Si]([O:8][CH2:9][C:10]1[CH:15]=[C:14]([O:16][CH2:17][CH3:18])[C:13]([F:19])=[C:12]([O:20][CH2:21][CH3:22])[CH:11]=1)(C)C)(C)(C)C>CO>[CH2:21]([O:20][C:12]1[CH:11]=[C:10]([CH2:9][OH:8])[CH:15]=[C:14]([O:16][CH2:17][CH3:18])[C:13]=1[F:19])[CH3:22]

Participants

3

Reactant 1

HCID 66912151Tert-butyl-(3,5-diethoxy-4-fluoro-benzyloxy)-dimethyl-silane

Product 1

HCID 59863043(3,5-Diethoxy-4-fluorophenyl)methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl-(3,5-diethoxy-4-fluoro-benzyloxy)-dimethyl-silane (1.20 g, 3.65 mmol, 1.0 equiv) in methanol (8 mL) was added Dowex 50W-X8 (0.33 g, cation exchange resin) and the reaction mixture stirred under Ar at rt for 22 h. The resin was removed by filtration and the reaction mixture concentrated by evaporation under reduced pressure yielding the title compound in quantitative yield (0.78 g). 1H NMR (400 MHz, CDCl3): S1.34 (t, J=7.0 Hz, 6H), 1.57 (t, J=5.4 Hz, 1H), 4.01 (q, J=7.0 Hz, 4H), 4.51 (d, J=5.4 Hz, 2H), 6.51 (d, J=6.8 Hz, 2H). MS (EI): 214.2 [M]+.

Workup

  1. customThe resin was removed by filtration
  2. concentrationthe reaction mixture concentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-6284f214eb174e24a9c1b7a596b1d701
Source dataset
uspto-grants-2010_07
Patent number
US07754744B2

Reaction notes

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