Water → 4-(2-Fluoropyridin-3-yl)cycloheptanone

HRID 410245Notes

Reaction equation

HRID 410245 reaction equation
[F:1][C:2]1[C:7]([CH:8]2[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]2)=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:15][Si](C=[N+]=[N-])(C)C.O>C(Cl)Cl>[F:1][C:2]1[C:7]([CH:8]2[CH2:15][CH2:9][CH2:10][C:11](=[O:14])[CH2:12][CH2:13]2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 167693TrimethylsilyldiazomethaneHCID 576067214-(2-Fluoropyridin-3-yl)cyclohexanone

Product 1

HCID 593271094-(2-Fluoropyridin-3-yl)cycloheptanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of boron trifluoride-diethyl etherate (0.64 g, 4.50 mmol) and 4-(2-fluoropyridin-3-yl)cyclohexanone (0.79 g, 4.09 mmol) in DCM (8 mL) at −25° C. under argon was added (trimethylsilyl)diazomethane (2.25 mL, 5.18 mmol, 2.0 M in hexanes). The reaction was stirred for 2 h at that temperature, water was added, and the mixture was extracted with DCM (2×). The combined organic extracts were washed with 10:1 saturated ammonium chloride/ammonium hydroxide mixture (1×), water (1×), saturated aqueous sodium chloride (1×), and dried over anhydrous magnesium sulfate. The mixture was filtered and the filtrate concentrated in vacuo. The resulting oil was purified by silica gel chromatography to give 4-(2-fluoropyridin-3-yl)cycloheptanone. MS (ESI, pos. ion) m/z: 208.1 (M+1).

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with DCM (2×)
  3. washThe combined organic extracts were washed with 10:1 saturated ammonium chloride/ammonium hydroxide mixture (1×), water (1×), saturated aqueous sodium chloride (1×)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe mixture was filtered
  6. concentrationthe filtrate concentrated in vacuo
  7. customThe resulting oil was purified by silica gel chromatography

Sources & evidence

ORD record
ord-923d152ccbd2499492e6817a0c585e3d
Source dataset
uspto-grants-2014_06
Patent number
US08759532B2

Reaction notes

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