Triethylsilane → 2-Fluoro-6-(oxiran-2-ylmethoxy)phenol

HRID 39017Notes

Reaction equation

HRID 39017 reaction equation
C([O:8][C:9]1[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:10]=1[O:11][CH2:12][CH:13]1[CH2:15][O:14]1)C1C=CC=CC=1.C([SiH](CC)CC)C>[Pd].C(O)C>[F:20][C:19]1[CH:18]=[CH:17][CH:16]=[C:10]([O:11][CH2:12][CH:13]2[CH2:15][O:14]2)[C:9]=1[OH:8]

Participants

5

Reactant 2

HCID 12052TriethylsilaneHCID 86652951HCID 86652951, compound

Product 1

HCID 866529502-Fluoro-6-(oxiran-2-ylmethoxy)phenolYield 65.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a mixture of 2-{[2-(benzyloxy)-3-fluorophenoxy]methyl}oxirane (8 g, 29.2 mmol), ethanol (65 ml) and Pd/C (0.5 g) under N2, triethylsilane (9.3 ml, 58.2 mmol) was added dropwise. The solution was stirred for 16 h at room temperature and filtered through Celite. The solvent was evaporated, Na2CO3 (10%) was added and the solution was extracted with EtOAc. The combined organic phases were dried (Na2SO4) and evaporated to dryness. Flash column chromatography (isooctane/EtOAc) yielded the title compound (3.5 g). MS m/z (rel. intensity, 70 eV) 184 (M+, bp), 153 (44), 139 (31), 128 (99), 57 (23).

Workup

  1. filtrationfiltered through Celite
  2. customThe solvent was evaporated
  3. additionNa2CO3 (10%) was added
  4. extractionthe solution was extracted with EtOAc
  5. dry with materialThe combined organic phases were dried (Na2SO4)
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-02408fa84554491daa271422eff6c4bb
Source dataset
uspto-grants-2013_09
Patent number
US08524766B2

Reaction notes

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