Hydrochloric Acid → 5-(Furan-3-carbonyl)-5,6-dihydro-cyclopenta[b]thiophen-4-one

HRID 532570

反応式

HRID 532570 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+].C([O:14][C:15]([C:17]1[CH:21]=[CH:20][O:19][CH:18]=1)=O)C.Cl>C1COCC1.C(OCC)(=O)C.O>[O:19]1[CH:20]=[CH:21][C:17]([C:15]([CH:7]2[CH2:8][C:2]3[S:1][CH:5]=[CH:4][C:3]=3[C:6]2=[O:9])=[O:14])=[CH:18]1

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 69201Ethyl 3-furoateHCID 19586324H,5H,6H-cyclopenta[b]thiophen-4-one

生成物 1

HCID 866992095-(Furan-3-carbonyl)-5,6-dihydro-cyclopenta[b]thiophen-4-one収率 27%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

5,6-Dihydro-cyclopenta[b]thiophen-4-one in 40 mL of THF was treated with NaH (60 percent, 0.8 g, 36.25 mmol). After the addition of Furan-3-carboxylic acid ethyl ester, 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 added with ethyl acetate (70 mL). 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-(Furan-3-carbonyl)-5,6-dihydro-cyclopenta[b]thiophen-4-one (0.9 g, 38 mmol) as brown solid in 27% yield.

後処理

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

出典と根拠

ORDレコード
ord-5e2c0907c9e04aee98ecf18bd0aa8f4d
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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