Cesium carbonate → 3-(3-Cyanophenyl)4-cyclobutyl-butan-2-one

HRID 133468

Reaction equation

HRID 133468 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH2:9][C:10]([CH3:12])=[O:11])[CH:6]=[CH:7][CH:8]=1)#[N:2].[CH:13]1(Br)[CH2:16][CH2:15][CH2:14]1.[C:18](=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[C:1]([C:3]1[CH:4]=[C:5]([CH:9]([CH2:18][CH:13]2[CH2:16][CH2:15][CH2:14]2)[C:10](=[O:11])[CH3:12])[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 78110BromocyclobutaneHCID 133549593-(2-Oxopropyl)benzonitrile

Product 1

HCID 222707633-(3-Cyanophenyl)4-cyclobutyl-butan-2-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 1.45 g (9.07 mmol) of 1-(3-cyanophenyl)acetone in 18 mL acetonitrile, 1.1 mL (9.5 mmol) cyclobutyl bromide and 5.91 g (18.1 mmol) cesium carbonate were added. After heating the solution in a 60° C. bath overnight, it was cooled and filtered. The filtrate was partitioned between water and EtOAc and the aqueous layer was extracted with EtOAc. The combined organic layer was washed with brine, dried and concentrated. The residue was purified on a flash column using a gradient of 5-10% EtOAc/hexane to isolate the title compound. 1H NMR: (500 MHz, CDCl3): δ 1.5-2.2 (m, 9H), 2.13 (s, 3H), 3.64 (m, 1H), 7.4-7.7 (m, 4H).

Workup

  1. temperaturewas cooled
  2. filtrationfiltered
  3. customThe filtrate was partitioned between water and EtOAc
  4. extractionthe aqueous layer was extracted with EtOAc
  5. washThe combined organic layer was washed with brine
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified on a flash column

Sources & evidence

ORD record
ord-3841bb69ed96442b9c4d3215c030ae57
Source dataset
uspto-grants-2008_06
Patent number
US07390835B2

Linked notes

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