Tetrahydrofuran → HCID 57796874、化合物

HRID 2099992ノート

反応式

HRID 2099992 の反応式
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]=[CH:11][C:12](Cl)=[O:13])=[CH:9][C:4]=2[O:3][CH2:2]1.COC(=O)[C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([NH2:26])[CH:21]=1)=[CH2:19].[C:28]([O-:31])(O)=[O:29].[Na+].O1CCC[CH2:34]1>O>[CH3:34][O:31][C:28](=[O:29])/[CH:19]=[CH:18]/[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([NH:26][C:12](=[O:13])/[CH:11]=[CH:10]/[C:8]2[CH:7]=[CH:6][C:5]3[O:1][CH2:2][O:3][C:4]=3[CH:9]=2)[CH:21]=1

参加物

6

反応物 4

HCID 8028Tetrahydrofuran2 回HCID 516892Sodium BicarbonateHCID 534112793-(2H-1,3-Benzodioxol-5-yl)prop-2-enoyl chlorideHCID 57495369HCID 57495369、化合物

生成物 1

HCID 57796874HCID 57796874、化合物収率 71%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

(Method G3) A solution of 3-benzo[1,3]dioxol-5-yl-acryloyl chloride (2a) (0.41 g, 1.95 mmol) in tetrahydrofuran (8.0 ml) was added to a mixture of m-aminophenylacrylic acid methyl ester (0.35 g, 1.97 mmol) in tetrahydrofuran (12.0 ml) and NaHCO3 (0.25 g, 3.00 mmol) in water (7.0 ml), and the resultant solution was stirred at room temperature for one hour. The reaction mixture was evaporated and the residue was partitioned between ethyl acetate and 2N HCl. The organic layer was washed successively with water, saturated NaCl, and dried (Na2SO4). The solvent was removed and the residue was chromatographed on silica gel with dichlormethane-methanol (40:1, v/v) as eluent. The obtained product was washed with diethyl ether to give the title compound (0.50 g, 71%). 1H NMR (DMSO-d6, HMDSO), δ: 3.73 (3H, s); 6.09 (2H, s); 6.49 (1H, d, J=16.0 Hz); 6.67 (1H, d, J=16.0 Hz); 6.89-7.83 (8H, m); 7.98 (1H, br s); 10.23 ppm (1H, br s)

後処理

  1. customThe reaction mixture was evaporated
  2. customthe residue was partitioned between ethyl acetate and 2N HCl
  3. washThe organic layer was washed successively with water, saturated NaCl
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was removed
  6. customthe residue was chromatographed on silica gel with dichlormethane-methanol (40:1
  7. washThe obtained product was washed with diethyl ether

出典と根拠

ORDレコード
ord-b56335c76cf249609ff9f72dc109b2fc
出典データセット
uspto-grants-2009_08
特許番号
US07569724B2

反応ノート

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