Hydrochloric Acid → 5-(4-Bromo-benzoyl)-5,6-dihydro-cyclopenta[b]thiophen-4-one

HRID 532534

反応式

HRID 532534 の反応式
[S:1]1[CH:5]=[CH:4][C:3]2[C:6](=[O:9])[CH2:7][CH2:8][C:2]1=2.[H-].[Na+].C1([O:18][C:19](=O)[C:20]2[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][CH:21]=2)C=CC=CC=1.Cl>C1COCC1.O>[Br:26][C:23]1[CH:24]=[CH:25][C:20]([C:19]([CH:7]2[CH2:8][C:2]3[S:1][CH:5]=[CH:4][C:3]=3[C:6]2=[O:9])=[O:18])=[CH:21][CH:22]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 530840Phenyl 4-bromobenzoateHCID 19586324H,5H,6H-cyclopenta[b]thiophen-4-one

生成物 1

HCID 866991945-(4-Bromo-benzoyl)-5,6-dihydro-cyclopenta[b]thiophen-4-one収率 70%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
100 °C

実験手順

5,6-Dihydro-cyclopenta[b]thiophen-4-one (3.34 g, 24.2 mmol) in 40 mL of THF was treated with NaH (60 percent, 1.45 g, 36.3 mmol). After the addition of 4-Bromo-benzoic acid phenyl ester (6.7 g, 24.2 mmol), the reaction mixture was heated at 100° C. for 8 hr. The solution was cooled to room temperature and poured into water. The resulting mixture was acidified with concentrated HCl and was extracted with ethyl acetate. The organic layer was collected, brined, dried over MgSO4(s), and concentrated under reduced pressure. The resultant precipitate was collected and recrystallized from ethanol to provide the corresponding 5-(4-Bromo-benzoyl)-5,6-dihydro-cyclopenta[b]thiophen-4-one (5.4 g, 16.9 mmol) as yellow solid in 70% yield.

後処理

  1. temperatureThe solution was cooled to room temperature
  2. extractionwas extracted with ethyl acetate
  3. customThe organic layer was collected
  4. dry with materialdried over MgSO4(s)
  5. concentrationconcentrated under reduced pressure
  6. customThe resultant precipitate was collected
  7. customrecrystallized from ethanol

出典と根拠

ORDレコード
ord-c0aa556a7a7648fcb7200d401f633a8e
出典データセット
uspto-grants-2014_10
特許番号
US08853207B2

関連ノート

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