Acetone → 3-Nitro-5-(1,2-dihydroxyethyl)benzoic acid methyl ester

HRID 383018ノート

反応式

HRID 383018 の反応式
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=C(C=C)[CH:7]=[C:6]([N+:12]([O-:14])=[O:13])[CH:5]=1.C[N+]1([O-])CC[O:20]CC1.Cl.[CH3:25][C:26]([CH3:28])=[O:27]>O.O=[Os](=O)(=O)=O>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:25]([CH:26]([OH:27])[CH2:28][OH:20])[CH:7]=[C:6]([N+:12]([O-:14])=[O:13])[CH:5]=1

参加物

7

反応物 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 82029Methyl morpholine oxideHCID 540267313-Nitro-5-vinylbenzoic acid methyl ester

生成物 1

HCID 545549833-Nitro-5-(1,2-dihydroxyethyl)benzoic acid methyl ester

試薬・触媒・溶媒 2

HCID 30318Osmium Tetroxide触媒HCID 962Water溶媒2 回

反応条件

温度
0 °C

実験手順

3-Nitro-5-vinylbenzoic acid methyl ester (2.02 g, 9.76 mmol) was dissolved in a mixture of acetone and water (200 ml, 9:1), and, after cooling to 0° C., OsO4 (60 mg, 0.24 mmol) was added followed by N-methylmorpholine-N-oxide (2.34 g, 20.0 mmol). After stirring for 46 h at room temperature, an aqueous solution of Na2S2O5 (3.7 g) in water (150 ml) was added and the solution was acidified with dilute aqueous HCl. The volume of the solution was reduced to 150 ml by evaporation and the residue was extracted with ethyl acetate (3×100 ml). The combined organic phases were evaporated and the residue was purified by column chromatography on silica gel using ethyl acetate as the eluent. Yield: 1.60 g (60%).

後処理

  1. customThe volume of the solution was reduced to 150 ml by evaporation
  2. extractionthe residue was extracted with ethyl acetate (3×100 ml)
  3. customThe combined organic phases were evaporated
  4. customthe residue was purified by column chromatography on silica gel

出典と根拠

ORDレコード
ord-fc2b20c9aea348edb2c694b4c5b328c9
出典データセット
uspto-grants-2001_10
特許番号
US06310243B1

反応ノート

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