Acetic Acid → 1-Benzyl-4-phenyl-1,2,3,6-tetrahydropyridine

HRID 276902ノート

反応式

HRID 276902 の反応式
[C:1]1([C:7]2[CH2:8][CH2:9][NH:10][CH2:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(O)(=O)C.C(OCC)(=O)C>ClC(Cl)C>[CH2:13]([N:10]1[CH2:9][CH:8]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:12][CH2:11]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 8857Ethyl AcetateHCID 825531,2,3,6-Tetrahydro-4-phenylpyridine

生成物 1

HCID 5636091-Benzyl-4-phenyl-1,2,3,6-tetrahydropyridine収率 50%

試薬・触媒・溶媒 1

HCID 63651,1-Dichloroethane溶媒

実験手順

1,2,3,6-Tetrahydro-4-phenylpyridine (410 mg, 2.6 mmol), benzaldehyde (300 mg, 2.9 mmol), sodium triacetoxyborate (1.1 g, 5.2 mmol) and acetic acid (1.5 ml, 26 mmol) were stirred in dichloroethane at a room temperature for 14 hours. To the reaction solution was added ethyl acetate, and the resulting solution was washed with sodium hydroxide aqueous solution (1 N) and saturated brine and dried with anhydrous sodium sulfate. Then the solvent was evaporated under a reduced pressure. Thereafter, the resulting residue was separated and purified by a silica gel column chromatography to obtain 330 mg of the title compound (1.3 mmol, 45% in yield).

後処理

  1. washthe resulting solution was washed with sodium hydroxide aqueous solution (1 N) and saturated brine
  2. dry with materialdried with anhydrous sodium sulfate
  3. customThen the solvent was evaporated under a reduced pressure
  4. customThereafter, the resulting residue was separated
  5. custompurified by a silica gel column chromatography

出典と根拠

ORDレコード
ord-d9ca1c3daf274125b95fbf68b4162893
出典データセット
uspto-grants-2002_03
特許番号
US06355642B1

反応ノート

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