Triethylsilane → 2-Ethyl-5-fluorophenol

HRID 2105064Notes

Reaction equation

HRID 2105064 reaction equation
C([SiH](CC)CC)C.[F:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=O)[CH3:16])=[C:11]([OH:18])[CH:10]=1>C(O)(C(F)(F)F)=O>[CH2:15]([C:12]1[CH:13]=[CH:14][C:9]([F:8])=[CH:10][C:11]=1[OH:18])[CH3:16]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 27373264'-Fluoro-2'-hydroxyacetophenone

Product 1

HCID 578037492-Ethyl-5-fluorophenolYield 65.9%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Triethylsilane (3.1 mL, 19.5 mmol) was added dropwise to a solution of 1-(4-fluoro-2-hydroxyphenyl)ethanone (1 g, 6.5 mmol) in TFA (13 mL). The mixture was stirred at ambient temperature and concentrated. Purification by flash chromatography (19:1, hexanes/EtOAc) afforded 600 mg of 2-ethyl-5-fluorophenol as a clear oil. Et3N (1.2 mL, 8.6 mmol) and TBSCl (715 mg, 4.7 mmol) were added to a solution of intermediate 386.2 (600 mg, 4.3 mmol) in CH2Cl2 and the solution was stirred overnight. Water was added to the mixture and it was extracted with CH2Cl2. The organics were combined, washed with brine, dried (Na2SO4) and concentrated. Purification by flash chromatography (hexanes) yielded 768 mg of Intermediate 386.3 as a clear oil. 1H NMR (400 MHz, CDCl3) δ ppm 0.23 (s, 6H) 1.01 (s, 9H) 1.15 (t, J=7.46 Hz, 3H) 2.55 (q, J=7.58 Hz, 2H) 6.49 (dd, J=10.52, 2.45 Hz, 1H) 6.59 (dt, J=8.38, 2.57 Hz, 1H) 7.01-7.08 (m, 1H).

Workup

  1. concentrationconcentrated
  2. customPurification by flash chromatography (19:1, hexanes/EtOAc)

Sources & evidence

ORD record
ord-9085fea7a9f34990a9a9a0a1ea575aa6
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

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