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

HRID 1275051

반응식

HRID 1275051 반응식
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]

참가 물질

5

반응물 4

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

생성물 1

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

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-592d5046b75a4bc3bbd6e7b836cf57c2
출처 데이터셋
uspto-grants-2000_12
특허 번호
US06159975

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