Dimethylformamide → Allyl 4-[(4-methoxybenzyl)oxy]-4-oxobutyl succinate

HRID 1766893

반응식

HRID 1766893 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)[CH2:21][CH2:22][C:23]([O:25]CC=C)=[O:24].C(N([CH2:35][CH3:36])CC)C.CN(C)[CH:39]=[O:40]>CN(C1C=CN=CC=1)C.C(OCC)(=O)C.CCCCCC>[C:2]([O:40][CH2:39][CH:35]=[CH2:36])(=[O:1])[CH2:3][CH2:4][C:5]([O:7][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH2:15][C:14]1[CH:17]=[CH:18][C:11]([O:10][CH3:9])=[CH:12][CH:13]=1)=[O:24])=[O:6]

참가 물질

9

반응물 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 699934-Methyloxybenzyl chlorideHCID 17862495Allyl 4-chloro-4-oxobutyrateHCID 23663870Sodium Oxybate

생성물 1

HCID 58885318Allyl 4-[(4-methoxybenzyl)oxy]-4-oxobutyl succinate수율 70%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 8058Hexane용매HCID 8857Ethyl Acetate용매2회

반응 조건

온도
100 °C

실험 절차

To a suspension of commercially available sodium 4-hydroxybutyrate (756 mg, 6.00 mmol) in N,N-dimethylformamide (10 ml) was added 4-methoxybenzyl chloride (987 mg, 6.30 mmol), and the mixture was heated at 100° C. for 3 hours. The reaction mixture was cooled, and allyl 4-chloro-4-oxobutyrate (1.06 g, 6.02 mmol) obtained from Example 14-(1), triethylamine (920 μl, 6.60 mmol), and 4-(N,N-dimethylamino)pyridine (10 mg) were added thereto at 0° C. The mixture was stirred at room temperature for 18 hours, and the obtained mixture was diluted with ethyl acetate, then the resulting solution was 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 solution was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to give an oily residue. The residue was subjected to chromatography on a silica gel (50 g) column (eluent; hexane:ethyl acetate=3:1˜2:1) to afford the title compound (1.52 g, 70% yield) as a colorless oil.

후처리

  1. temperatureThe reaction mixture was cooled
  2. customat 0° C
  3. washthe resulting solution was washed successively with water
  4. dry with materialThe solution was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customto give an oily residue

출처 및 근거

ORD 기록
ord-6a6751f01a83454a82f29511a6fe7c60
출처 데이터셋
uspto-grants-2007_06
특허 번호
US07230023B2

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