Hexane → 4-Methoxybenzyl 4-(allyloxycarbonyloxy)butyrate

HRID 1766886

반응식

HRID 1766886 반응식
[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]

참가 물질

9

반응물 4

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

생성물 1

HCID 178625304-Methoxybenzyl 4-(allyloxycarbonyloxy)butyrate수율 62%

시약·촉매·용매 4

HCID 142844-(Dimethylamino)pyridine촉매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매3회

반응 조건

온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-fc547d44ddf6439889f4d47c3b3815ca
출처 데이터셋
uspto-grants-2007_06
특허 번호
US07230023B2

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