Hydrochloric Acid → (R)-3-(3,5-dimethylbenzoyl)-4-methyldihydrofuran-2-one

HRID 1275051ノート

反応式

HRID 1275051 の反応式
CO[C:3](=[O:12])[C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([CH3:11])[CH:5]=1.[OH-].[Na+].Cl.[CH3:16][C@H:17]1[CH2:21][O:20][C:19](=[O:22])[CH2:18]1>>[CH3:10][C:8]1[CH:9]=[C:4]([CH:5]=[C:6]([CH3:11])[CH:7]=1)[C:3]([C@H:18]1[CH:17]([CH3:16])[CH2:21][O:20][C:19]1=[O:22])=[O:12]

参加物

5

反応物 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 32786Benzoic acid, 3,5-dimethyl-, methyl esterHCID 5325910(R)-4-Methyldihydrofuran-2(3H)-one

生成物 1

HCID 53860757(R)-3-(3,5-dimethylbenzoyl)-4-methyldihydrofuran-2-one収率 62.1%

実験手順

To a solution of (R)-4-methyldihydrofuran-2-one (1.68 g in 40 mL dioxane) were added 5.51 g 3,5-dimethylbenzoic acid methyl ester followed by 1.82 g sodium hydroxide and the mixture heated to reflux on an oil bath. After 3 hours, the mixture was cooled to room temperature and the pH neutralized by the addition of 0.5N hydrochloric acid. The mixture was then extracted with ethyl acetate and the organic portion washed with brine and dried over sodium sulfate. Purification of the concentrate by flash chromatography on silica gel (hexane:ethyl acetate, 9:1) gave the title compound (2.42 g).

後処理

  1. temperaturethe mixture heated
  2. temperatureto reflux on an oil bath
  3. extractionThe mixture was then extracted with ethyl acetate
  4. washthe organic portion washed with brine
  5. dry with materialdried over sodium sulfate
  6. customPurification of the
  7. concentrationconcentrate by flash chromatography on silica gel (hexane:ethyl acetate, 9:1)

出典と根拠

ORDレコード
ord-592d5046b75a4bc3bbd6e7b836cf57c2
出典データセット
uspto-grants-2000_12
特許番号
US06159975

反応ノート

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