Hexane → 4-Methoxybenzyl 4-(allyloxycarbonyloxy)butyrate

HRID 1766886

反応式

HRID 1766886 の反応式
[OH:1][CH2:2][CH2:3][CH2:4][C:5]([O-:7])=[O:6].[Na+].[CH3:9][O:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15]Cl)=[CH:13][CH:12]=1.Cl[C:20]([O:22][CH2:23][CH:24]=[CH2:25])=[O:21].CCCCCC>CN(C)C=O.C(OCC)(=O)C.ClCCl.CN(C1C=CN=CC=1)C>[CH2:23]([O:22][C:20]([O:1][CH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:15][C:14]1[CH:17]=[CH:18][C:11]([O:10][CH3:9])=[CH:12][CH:13]=1)=[O:6])=[O:21])[CH:24]=[CH2:25]

参加物

9

反応物 4

HCID 8058HexaneHCID 18052Allyl chloroformateHCID 699934-Methyloxybenzyl chlorideHCID 23663870Sodium Oxybate

生成物 1

HCID 178625304-Methoxybenzyl 4-(allyloxycarbonyloxy)butyrate収率 62%

試薬・触媒・溶媒 4

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒3 回

反応条件

温度
100 °C

実験手順

To a suspension of commercially available sodium 4-hydroxybutyrate (10.3 g, 81.7 mmol) in N,N-dimethylformamide (80 ml) was added 4-methoxybenzyl chloride (12.8 g, 81.7 mmol), and the mixture was heated at 100° C. for 1 hour. After cooling, the mixture was diluted with ethyl acetate, and the resulting solution was washed three times with water and once with an aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to give a colorless, oily residue. The residue was dissolved in dichloromethane (150 ml), and 4-(N,N-dimethylamino)pyridine (11.0 g, 90 mmol) and allyl chloroformate (9.85 g, 81.7 mmol) were added thereto at 0° C., and the resulting mixture was stirred at room temperature for 16 hours. The mixture was diluted with ethyl acetate, then washed successively with water, a saturated aqueous solution of sodium hydrogen carbonate, a saturated aqueous solution of ammonium chloride, and an aqueous solution of sodium chloride. The extract was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to afford an oily residue. The residue was subjected to chromatography on a silica gel (600 g) column (eluent; ethyl acetate:hexane=4:1˜2:1) to afford the title compound (15.61 g, 62% yield) as a colorless oil.

後処理

  1. temperatureAfter cooling
  2. washthe resulting solution was washed three times with water
  3. dry with materialonce with an aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customto give a colorless, oily residue
  6. washwashed successively with water
  7. dry with materialThe extract was dried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customto afford an oily residue

出典と根拠

ORDレコード
ord-fc547d44ddf6439889f4d47c3b3815ca
出典データセット
uspto-grants-2007_06
特許番号
US07230023B2

関連ノート

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