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

HRID 913320Notes

Reaction equation

HRID 913320 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): δ 1.34 (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-0c1c232296f04b6691a554bd6b38c88c
Source dataset
uspto-grants-2011_09
Patent number
US08026365B2

Reaction notes

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