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Sodium Hydroxide → HCID 21110471、化合物

HRID 1766935
ノート
印刷プレビュー

反応式

HRID 1766935 の反応式
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]#[N:12])[CH:9]=2)[CH2:4][O:3]1.[OH-:13].[Na+].[CH3:15][O:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Cl)=[CH:19][CH:18]=1.Cl[C:26]([O:28][CH2:29][CH:30]=[CH2:31])=[O:27]>O1CCCC1CO.CN(C1C=CN=CC=1)C.C(OCC)(=O)C.CCCCCC.ClCCl>[CH2:29]([O:28][C:26]([O:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]#[N:12])=[CH:9][C:10]=1[C:2]([O:1][CH2:21][C:20]1[CH:23]=[CH:24][C:17]([O:16][CH3:15])=[CH:18][CH:19]=1)=[O:13])=[O:27])[CH:30]=[CH2:31]
参加物実験手順後処理出典と根拠反応ノート

参加物

10

反応物 4

HCID 14798Sodium HydroxideHCID 18052Allyl chloroformateHCID 699934-Methyloxybenzyl chlorideHCID 132895623-Oxo-1,3-dihydroisobenzofuran-5-carbonitrile

生成物 1

HCID 21110471HCID 21110471、化合物収率 46.9%

試薬・触媒・溶媒 5

HCID 142844-(Dimethylamino)pyridine
触媒
HCID 6344Dichloromethane溶媒
HCID 7360Tetrahydrofurfuryl alcohol溶媒
HCID 8058Hexane溶媒
HCID 8857Ethyl Acetate溶媒2 回

実験手順

1-Oxo-1,3-dihydroisobenzofuran-6-carbonitrile (3.01 g, 18.9 mmol) obtained from Example 5-(2) was dissolved in a mixed solvent (200 ml) of tetrahydrofuran-methanol (3:1), and an aqueous solution of sodium hydroxide (1.004N; 17.4 ml, 17.4 mmol) was added thereto over a period of 10 minutes. The mixture was stirred at room temperature for 30 minutes, and the solvent was distilled off under reduced pressure. The resulting residue was dried using a vacuum pump. The obtained solid was dissolved in N,N-dimethylformamide (40 ml), and 4-methoxybenzyl chloride (2.96 g, 18.9 mmol) was added thereto. The mixture was heated at 70-80° C. for 1 hour. After cooling the mixture to 0° C., dichloromethane (40 ml) was added thereto, and 4-(N,N-dimethylamino)pyridine (5.78 g, 47.3 mmol) and allyl chloroformate (4.56 g, 37.9 mmol) were added thereto, then the mixture was stirred at the same temperature for 30 minutes. The mixture was diluted with ethyl acetate and then washed successively with water and an aqueous solution of sodium chloride. The resulting mixture 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 (100 g) column (eluent; hexane:ethyl acetate=3:1) to afford the title compound (3.11 g, 43% yield) as a colorless oil.

後処理

  1. distillationthe solvent was distilled off under reduced pressure
  2. customThe resulting residue was dried
  3. dissolutionThe obtained solid was dissolved in N,N-dimethylformamide (40 ml)
  4. temperatureThe mixture was heated at 70-80° C. for 1 hour
  5. temperatureAfter cooling the mixture to 0° C.
  6. stirringthe mixture was stirred at the same temperature for 30 minutes
  7. washwashed successively with water
  8. dry with materialThe resulting mixture was dried over anhydrous magnesium sulfate
  9. distillationthe solvent was distilled off under reduced pressure
  10. customto give an oily residue

出典と根拠

ORDレコード
ord-18b7f0ef30864a6999f2889420e83ed1
出典データセット
uspto-grants-2007_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07230023B2

反応ノート

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