Dibenzylamine → 1-Acetoxy-4-dibenzylamino-2-butene

HRID 275214ノート

反応式

HRID 275214 の反応式
[CH2:1]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16]([O:19][CH2:20][CH:21]=[CH:22][CH2:23]OC(=O)C)(=[O:18])[CH3:17]>O1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:16]([O:19][CH2:20][CH:21]=[CH:22][CH2:23][N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:18])[CH3:17]

参加物

5

反応物 2

HCID 7656DibenzylamineHCID 1404022-Butene-1,4-diol diacetate

生成物 1

HCID 537897791-Acetoxy-4-dibenzylamino-2-butene

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of dibenzylamine (40 g, 0.2 mol) and 2-butene-1,4-diol diacetate (105 g, 0.61 mol) dissolved in 150 ml of tetrahydrofuran (THF) is treated with tetrakis(triphenylphosphine)palladium(0) (1.0 g, 0.9 mmol) and stirred at room temperature overnight. The reaction mixture is concentrated in vacuo and the excess 2-butene-1,4-diol diacetate is removed by bulb-to-bulb distillation at 80°-90° C./1 mm. The residue is purified by eluting through a short plug of silica gel (1:1 ethyl acetate:hexanes). 1-Acetoxy-4-dibenzylamino-2-butene is obtained in a yield of 59.2 g (95%).

後処理

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. customthe excess 2-butene-1,4-diol diacetate is removed by bulb-to-bulb distillation at 80°-90° C./1 mm
  3. customThe residue is purified
  4. washby eluting through a short plug of silica gel (1:1 ethyl acetate:hexanes)

出典と根拠

ORDレコード
ord-a806bdfc680c4b62b52a92b96fd76cfc
出典データセット
uspto-grants-1995_02
特許番号
US05391808

反応ノート

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