2-Butene-1,4-diol → 1,4-Bis(4-methoxybenzyloxy)but-2-ene

HRID 1089255

反応式

HRID 1089255 の反応式
[CH2:1]([OH:6])[CH:2]=[CH:3][CH2:4][OH:5].[H-].[Na+].[CH3:9][O:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15]Cl)=[CH:13][CH:12]=1>CN(C)C=O>[CH3:9][O:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][O:5][CH2:4][CH:3]=[CH:2][CH2:1][O:6][CH2:15][C:14]2[CH:17]=[CH:18][C:11]([O:10][CH3:9])=[CH:12][CH:13]=2)=[CH:13][CH:12]=1

参加物

5

反応物 3

HCID 80652-Butene-1,4-diolHCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chloride

生成物 1

HCID 545551371,4-Bis(4-methoxybenzyloxy)but-2-ene収率 70%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

To a solution of 2-buten-1,4-diol (4.9 g, 60 mmol) in dry dimethylformamide (120 ml) was added sodium hydride (60% dispersion in oil; 5.28 g, 132 mmol) and the mixture was stirred at room temperature for 100 minutes. To this solution was added 4-methoxybenzyl chloride (17.9 ml, 132 mmol) in dimethylformamide (30 ml) dropwise over 45 minutes and the mixture was stirred for a further 40 minutes. The mixture was partitioned between ether (150 ml) and water (150 ml). The organic layer was further washed with water (150 ml), dried (magnesium sulphate) and the solvent was removed. The residue was purified by column chromatography on silica gel eluting with hexane-acetone (4:1, 3:1) to afford 1,4-bis(4-methoxybenzyloxy)but-2-ene as a clear colourless liquid (13.7 g, 70%). IR: υmax (film) 2840, 1615, 1515 and 1250 cm-1. 1H NMR: δH (CDCl3) 3.80 (6H, s, 2×CH3), 4.02 (4H, d, J=4.5 Hz, 2×CHCH2), 4.43 (4H, s, 2×ArCH2), 5.79 (2H, t, J=4.5 Hz, 2×CH), 6.88 (4H, d, J=9 Hz, ArH) and 7.27 (4H, d, J=9 Hz, ArH).

後処理

  1. stirringthe mixture was stirred for a further 40 minutes
  2. customThe mixture was partitioned between ether (150 ml) and water (150 ml)
  3. washThe organic layer was further washed with water (150 ml)
  4. dry with materialdried (magnesium sulphate)
  5. customthe solvent was removed
  6. customThe residue was purified by column chromatography on silica gel eluting with hexane-acetone (4:1, 3:1)

出典と根拠

ORDレコード
ord-7012a792d1d44d4a9d86aaa7bc5c10f1
出典データセット
uspto-grants-1990_10
特許番号
US04965270

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