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Hydrochloric Acid → (2S)-2-(2,4-Difluorophenyl)-2-oxiranemethanol

HRID 1003781
ノート
印刷プレビュー

反応式

HRID 1003781 の反応式
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@@:9]([OH:23])([CH2:17][O:18]S(C)(=O)=O)[CH2:10]OC(=O)C(C)C.[OH-].[Na+].Cl>CO>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]1([O:23][CH2:10]1)[CH2:17][OH:18]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 11279597(S)-2-(2,4-difluorophenyl)-1-isobutyryloxy-3-methanesulfonyloxy-2-propanol

生成物 1

HCID 10176425(2S)-2-(2,4-Difluorophenyl)-2-oxiranemethanol収率 95.1%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

In 14 ml of methanol was dissolved 4.06 g of (S)-2-(2,4-difluorophenyl)-1-isobutyryloxy-3-methane-sulfonyloxy-2-propanol obtained in Example 44. After a temperature of the resulting liquid was kept at 5° C, 14 ml of aqueous solution of 2N sodium hydroxide was added dropwise thereto with cooling at 15° C. or below. After dropping, the resulting liquid was stirred at a temperature of 10° to 15° C. for 2 hours. Thereto 1N hydrochloric acid was added until the liquid was adjusted to pH 7 and methanol was removed under reduced pressure. To the residue was added ethyl acetate to extract. The resulting organic layer was washed with saturated aqueous solution with sodium chloride. The solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel (eluent n-hexane/ethyl acetate=1/1) to give 2.04 g of oily (S)-2-(2,4-difluorophenyl)-2,3-epoxy-1-propanol. An optical purity thereof was determined in the same manner as in Example 35. (Elution time: 9.24 minutes ((S)-form) and 10.7 minutes ((R)-form)).

後処理

  1. customwas kept at 5° C
  2. temperaturewith cooling at 15° C. or below
  3. customwas removed under reduced pressure
  4. additionTo the residue was added ethyl acetate
  5. extractionto extract
  6. washThe resulting organic layer was washed with saturated aqueous solution with sodium chloride
  7. customThe solvent was removed under reduced pressure
  8. customthe residue was purified by column chromatography on silica gel (eluent n-hexane/ethyl acetate=1/1)

出典と根拠

ORDレコード
ord-75012ad5db284f8a962a8d90973d0271
出典データセット
uspto-grants-2000_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06046354

反応ノート

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