Triethylamine → 6-(4-benzoylbenzoyl)-5,6,7,8-tetrahydro-4H-furo[2,3-d]azepine

HRID 611227ノート

反応式

HRID 611227 の反応式
Cl.[O:2]1[C:6]2[CH2:7][CH2:8][NH:9][CH2:10][CH2:11][C:5]=2[CH:4]=[CH:3]1.[C:12]([C:20]1[CH:28]=[CH:27][C:23]([C:24](O)=[O:25])=[CH:22][CH:21]=1)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C.C(P(=O)(OCC)OCC)#N.[OH-].[Na+]>ClCCl>[C:12]([C:20]1[CH:21]=[CH:22][C:23]([C:24]([N:9]2[CH2:10][CH2:11][C:5]3[CH:4]=[CH:3][O:2][C:6]=3[CH2:7][CH2:8]2)=[O:25])=[CH:27][CH:28]=1)(=[O:19])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

参加物

7

反応物 5

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 691474-Benzoylbenzoic acidHCID 76257Diethyl cyanophosphonateHCID 196002485,6,7,8-Tetrahydro-4H-furo[2,3-d]azepine Hydrochloride

生成物 1

HCID 196001536-(4-benzoylbenzoyl)-5,6,7,8-tetrahydro-4H-furo[2,3-d]azepine

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 0.128 g of the above crude 5,6,7,8-tetrahydro-4H-furo[2,3-d]azepine hydrochloride, 0.22 g (0.97 mmol) of 4-benzoylbenzoic acid and 0.45 ml (3.2 mmol) of triethylamine in 30 ml of dichloromethane, 0.15 ml (0.97 mmol) of diethyl cyanophosphonate was added dropwise under ice-cooling, followed by overnight stirring at room temperature. The reaction mixture was poured into aqueous sodium hydroxide and extracted with dichloromethane 3 times. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=3/1 to 1/1) to yield the desired product.

後処理

  1. temperaturecooling
  2. extractionextracted with dichloromethane 3 times
  3. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=3/1 to 1/1)

出典と根拠

ORDレコード
ord-cbd87fcce67142c6aedcd24c54a1088d
出典データセット
uspto-grants-1999_12
特許番号
US05998433

反応ノート

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