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

HRID 502383Notes

Reaction equation

HRID 502383 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 eq.) in methanol (8 mL) was added Dowex 50W-X8 (0.33 g) 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): δ1.34 (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: 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-c5c9a6d686604d2f802ad16b83639dde
Source dataset
uspto-grants-2010_08
Patent number
US07772253B2

Reaction notes

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