Diethyl Ether → Ethanone, 1-(3,3-difluorocyclopentyl)-

HRID 1177528Notes

Reaction equation

HRID 1177528 reaction equation
[F:1][C:2]1([F:13])[CH2:6][CH2:5][CH:4]([C:7](N(OC)C)=[O:8])[CH2:3]1.[CH3:14][Mg]Br.C(OCC)C>C1COCC1>[F:1][C:2]1([F:13])[CH2:6][CH2:5][CH:4]([C:7](=[O:8])[CH3:14])[CH2:3]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 53403834HCID 53403834, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 67111687Ethanone, 1-(3,3-difluorocyclopentyl)-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (rac)-3,3-difluoro-N-methoxy-N-methylcyclopentane-carboxamide (1.90 g, 9.83 mmol) in 20 mL THF at 0° C. was added methylmagnesium bromide 3.0 m in diethyl ether (6.56 mL, 19.67 mmol) slowly dropwise. The reaction mixture became white and cloudy. After 1.5 h, the reaction mixture was quenched carefully with ice and 1N HCl, and diluted with Et2O. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo to give (rac)-1-(3,3-difluorocyclopentyl)ethanone as a light yellow oil. 1H NMR (400 MHz, CDCl3-d) δ ppm 3.03-3.19 (m, 1 H), 2.22-2.48 (m, 2 H), 2.20 (s, 3 H), 2.03-2.16 (m, 3 H), 1.90-1.99 (m, 1 H).

Workup

  1. customthe reaction mixture was quenched carefully with ice and 1N HCl
  2. additiondiluted with Et2O
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bc6f029ec797486ea718974061523339
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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