1,3-Indandione → 2-(3-Chlorobenzoyl)-1,3-indanedione

HRID 393914

反応式

HRID 393914 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[C:5]([O:7]C1C=CC([N+]([O-])=O)=CC=1)=O.[C:20]1(=[O:30])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22](=[O:29])[CH2:21]1.[F-].[K+]>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[C:5]([CH:21]1[C:20](=[O:30])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]1=[O:29])=[O:7]

参加物

4

反応物 3

HCID 118151,3-IndandioneHCID 522689Potassium FluorideHCID 81083104-Nitrophenyl 3-chlorobenzoate

生成物 1

HCID 226483342-(3-Chlorobenzoyl)-1,3-indanedione収率 160.4%

反応条件

温度
80 °C

実験手順

A 25-mL 3-neck round bottom flask was charged with 4-nitrophenyl 3-chlorobenzoate (0.64 g, 2.3 mmol), indane-1,3-dione (0.39 g, 2.7mmol) and (methyl sulfoxide)-d6 (5.0 g). The mixture was heated to 80° C. and potassium fluoride (0.60 g, 10 mmol) was added in a single portion. After stirring at 80° C. for 7 hours, the mixture was cooled, partitioned between diethyl ether-ethyl acetate (1:1, 100 mL) and 1N hydrochloric acid (25 mL). The organic layer was washed with additional portions of 1N hydrochloric acid (3×10 mL), then with brine (10 mL), dried over magnesium sulfate, filtered, and evaporated to leave a brown solid (1.05 g).

後処理

  1. temperaturethe mixture was cooled
  2. custompartitioned between diethyl ether-ethyl acetate (1:1, 100 mL) and 1N hydrochloric acid (25 mL)
  3. washThe organic layer was washed with additional portions of 1N hydrochloric acid (3×10 mL)
  4. dry with materialwith brine (10 mL), dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

出典と根拠

ORDレコード
ord-1eca2e867ee748e2b23a146c22192fb4
出典データセット
uspto-grants-2004_10
特許番号
US06809206B2

関連ノート

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