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Ethyl Acetate → Diethyl (7,8-difluoro-3-methyl-3,4-dihydro-2H-[1,4]benzoxazine-4-yl)methylenemalonate

HRID 1034035
ノート
印刷プレビュー

反応式

HRID 1034035 の反応式
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([NH:9][CH:10]=[C:11]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:3]=1[O:22][CH2:23][CH:24](OS(C1C=CC(C)=CC=1)(=O)=O)[CH3:25].C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1.C(OCC)(=O)C>CN(C)C=O.O>[F:8][C:7]1[CH:6]=[CH:5][C:4]2[N:9]([CH:10]=[C:11]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:24]([CH3:25])[CH2:23][O:22][C:3]=2[C:2]=1[F:1]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 146971842,3-Difluoro-6-(2,2-diethoxycarbonylethenyl)amino-[(2-p-toluenesulfonyloxypropyl)oxy]benzene

生成物 1

HCID 13364401Diethyl (7,8-difluoro-3-methyl-3,4-dihydro-2H-[1,4]benzoxazine-4-yl)methylenemalonate

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
80 °C

実験手順

To a solution of 791 mg of the compound obtained in Example 4 in 5 ml of anhydrous N,N-dimethylformamide (hereinafter abbreviated as DMF), 207 mg of potassium carbonate and a catalytic amount of 18-crown-6-ether were added, and the mixture was heated at 80° C. for 8.5 hours. To the mixture were added ethyl acetate and water. The mixture was shaken, and the organic layer was separated. The organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified through silica gel column chromatography to yield the titled compound as crystals in quantitative yield. The physical data of the product were identical to those of the authentic specimen as described in Reference Example B-1.

後処理

  1. customthe organic layer was separated
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customThe residue was purified through silica gel column chromatography

出典と根拠

ORDレコード
ord-f0574e6c87b8428b9e9d7b5c741ab07b
出典データセット
uspto-grants-1994_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05312999

反応ノート

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