5-Fluoro-1-indanone → 1-Ethyl-5-fluoroindan-1-ol

HRID 561459Notes

Reaction equation

HRID 561459 reaction equation
[CH2:1]([Mg]Br)[CH3:2].[F:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[CH2:10][CH2:9]2>C(OCC)C>[CH2:1]([C:11]1([OH:15])[C:12]2[C:8](=[CH:7][C:6]([F:5])=[CH:14][CH:13]=2)[CH2:9][CH2:10]1)[CH3:2]

Participants

4

Reactant 2

HCID 1365375-Fluoro-1-indanoneHCID 178418443HCID 178418443, compound

Product 1

HCID 593404281-Ethyl-5-fluoroindan-1-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

292 ml (876 mmol) of a 3N solution of ethylmagnesium bromide in diethyl ether were added to 5.00 g (33.3 mmol) of 5-fluoroindan-1-one in 150 ml of diethyl ether at RT, and the mixture was stirred at RT overnight. The reaction mixture was added to a saturated, ice-cold aqueous ammonium chloride solution, the phases were separated, the aqueous phase was extracted with dichloromethane, and the combined organic phases were dried over magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography on silica gel (mobile phase: toluene/ethyl acetate gradient) to result in 5.70 g (94% of theory) of the title compound.

Workup

  1. additionThe reaction mixture was added to a saturated, ice-cold aqueous ammonium chloride solution
  2. customthe phases were separated
  3. extractionthe aqueous phase was extracted with dichloromethane
  4. dry with materialthe combined organic phases were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography on silica gel (mobile phase: toluene/ethyl acetate gradient)

Sources & evidence

ORD record
ord-426c56f0593145df88a405aacc30b57f
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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