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

HRID 133468

反応式

HRID 133468 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
60 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-3841bb69ed96442b9c4d3215c030ae57
出典データセット
uspto-grants-2008_06
特許番号
US07390835B2

関連ノート

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