Water → Methyl 2-(9-chloro-8-oxononyloxy)-2-methylpropionate

HRID 1796357ノート

反応式

HRID 1796357 の反応式
[Cl:1][CH2:2][CH:3]([OH:19])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]([CH3:18])([CH3:17])[C:13]([O:15][CH3:16])=[O:14].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.S(=O)(=O)(O)O.O>CC(C)=O.C(O)(C)C>[Cl:1][CH2:2][C:3](=[O:19])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]([CH3:17])([CH3:18])[C:13]([O:15][CH3:16])=[O:14]

参加物

7

反応物 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 21866631Methyl 2-(9-chloro-8-hydroxynonyloxy)-2-methylpropionateHCID 131709961Jones' reagent2 回

生成物 1

HCID 21866630Methyl 2-(9-chloro-8-oxononyloxy)-2-methylpropionate収率 59%

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 3776Isopropanol溶媒

実験手順

Methyl 2-(9-chloro-8-hydroxynonyloxy)-2-methylpropionate (31 g) was dissolved in 465 ml of acetone, and 46 ml of Jones reagent prepared by adding 10.2 ml of conc. sulfuric acid and 12 g of chromic (VI) oxide to 45 ml of water was added dropwise with stirring under ice-cooling. After 3-hour-stirring at room temperature, an excess amount of Jones reagent was decomposed by adding isopropyl alcohol, The reaction mixture was poured into ice-cold water, extracted with ethyl acetate, washed with brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane:ethyl acetate=7.5:1) to provide 18.16 g of the objective compound as oil.

後処理

  1. additionwas added dropwise
  2. temperaturecooling
  3. stirringAfter 3-hour-stirring at room temperature
  4. additionThe reaction mixture was poured into ice-cold water
  5. extractionextracted with ethyl acetate
  6. washwashed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane:ethyl acetate=7.5:1)

出典と根拠

ORDレコード
ord-938d90b548a747d982b34cb63b9bd352
出典データセット
uspto-grants-2006_04
特許番号
US07030143B2

反応ノート

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