Lithium aluminum hydride → 3,3-Diphenyl-2-propen-1-amine

HRID 2190324

反応式

HRID 2190324 の反応式
[C:1]1([C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][C:9]#[N:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-].[Al+3].[Cl-].[Cl-].[AlH4-].[Li+]>C1COCC1>[C:11]1([C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:8][CH2:9][NH2:10])[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

参加物

5

反応物 3

HCID 28112Lithium aluminum hydrideHCID 2743523,3-DiphenylacrylonitrileHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 413783,3-Diphenyl-2-propen-1-amine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
40 °C

実験手順

To a solution of 3,3-diphenylacrylonitrile (4.45 g, 21.7 mmol) in THF (75 mL) at 0° C. was added aluminum(III) chloride (3.27 g, 24.5 mmol) and lithium tetrahydroaluminate (1 M in THF) (0.910 g, 24.0 mmol) (24 mL). The reaction mixture was warmed to room temperatrue and stirred for 1 h, heated to 40° C. for 2 h, heated to 60° C. for 2 h, quenched with water (5 mL), adjusted to pH 12 with ammonium hydroxide, diluted with brine, and EtOAc, extracted with EtOAc (5×), combined organic extracts washed with brine (1×), dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (eluted with 3% to 10% MeOH (2 M NH3) in DCM) gave 3,3-diphenyl-2-propenylamine.

後処理

  1. temperatureThe reaction mixture was warmed to room temperatrue
  2. temperatureheated to 60° C. for 2 h
  3. customquenched with water (5 mL)
  4. additiondiluted with brine, and EtOAc
  5. extractionextracted with EtOAc (5×)
  6. washcombined organic extracts washed with brine (1×)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification by flash column chromatography on silica gel (eluted with 3% to 10% MeOH (2 M NH3) in DCM)

出典と根拠

ORDレコード
ord-911f36b51e62459e9a7107784939e5d4
出典データセット
uspto-grants-2012_12
特許番号
US08324396B2

関連ノート

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