Triethylamine → 5-[4-(4-Methoxybenzoyl)benzoyl]-4,5,6,7-tetrahydrofuro[3,2-c]pyridine

HRID 611261ノート

反応式

HRID 611261 の反応式
Cl.[O:2]1[C:10]2[CH2:9][CH2:8][NH:7][CH2:6][C:5]=2[CH:4]=[CH:3]1.[CH3:11][O:12][C:13]1[CH:29]=[CH:28][C:16]([C:17]([C:19]2[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[CH:21][CH:20]=2)=[O:18])=[CH:15][CH:14]=1.C(N(CC)CC)C.C(P(=O)(OCC)OCC)#N>ClCCl.O>[CH3:11][O:12][C:13]1[CH:29]=[CH:28][C:16]([C:17]([C:19]2[CH:27]=[CH:26][C:22]([C:23]([N:7]3[CH2:8][CH2:9][C:10]4[O:2][CH:3]=[CH:4][C:5]=4[CH2:6]3)=[O:24])=[CH:21][CH:20]=2)=[O:18])=[CH:15][CH:14]=1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 177891814-(4-Methoxybenzoyl)benzoic acidHCID 195999414,5,6,7-Tetrahydrofuro[3,2-c]pyridine hydrochloride

生成物 1

HCID 196002365-[4-(4-Methoxybenzoyl)benzoyl]-4,5,6,7-tetrahydrofuro[3,2-c]pyridine

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 0.160 g (1.000 mmol) of 4,5,6,7-tetrahydrofuro[3,2-c]pyridine hydrochloride, 0.308 g (1.2 mmol) of 4-(4-methoxybenzoyl)benzoic acid and 0.55 ml (4.0 mmol) of triethylamine in 30 ml of dichloromethane, 0.24 g (1.5 mmol) of diethyl cyanophosphonate was added dropwise under ice-cooling, followed by overnight stirring at room temperature. The reaction mixture was poured into water and extracted with dichloromethane 2 times. The combined organic layer was washed with water and 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=2/1) to yield the desired product.

後処理

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

出典と根拠

ORDレコード
ord-e55a2e28889b490ca7a869d6d1424857
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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