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

HRID 1766893

反応式

HRID 1766893 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)[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]

参加物

9

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒2 回

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6a6751f01a83454a82f29511a6fe7c60
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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