Triethylamine → 1-(6,7-dihydro-4H-furo[3,2-c]pyridin-5-yl)-6-phenylhexan-1-one

HRID 611090

反応式

HRID 611090 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.[C:11]1([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22](O)=[O:23])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C.C(P(=O)(OCC)OCC)#N.[OH-].[Na+]>ClCCl>[O:2]1[C:10]2[CH2:9][CH2:8][N:7]([C:22](=[O:23])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:6][C:5]=2[CH:4]=[CH:3]1

参加物

7

反応物 5

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 76257Diethyl cyanophosphonateHCID 796956-Phenylhexanoic AcidHCID 195999414,5,6,7-Tetrahydrofuro[3,2-c]pyridine hydrochloride

生成物 1

HCID 196000411-(6,7-dihydro-4H-furo[3,2-c]pyridin-5-yl)-6-phenylhexan-1-one

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 0.250 g (1.566 mmol) of 4,5,6,7-tetrahydrofuro[3,2-c]pyridine hydrochloride, 0.33 g (1.7 mmol) of 6-phenylhexanoic acid and 0.87 ml (6.3 mmol) of triethylamine in 30 ml of dichloromethane, 0.36 ml (2.4 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 chromatography (hexane/ethyl acetate=6/1 to 3/1) 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 chromatography (hexane/ethyl acetate=6/1 to 3/1)

出典と根拠

ORDレコード
ord-6ec201416ced41c4bad2f6ecf37c45df
出典データセット
uspto-grants-1999_12
特許番号
US05998433

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