Ammonium Acetate → 1-[4-(1,1-Dimethylethyl)-2-methyl-5-oxazolyl]-2,2-dimethyl-1-propanone

HRID 1647413노트

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HRID 1647413 반응식
[C:1]([O:4][CH:5]([C:12](=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14])[C:6](=O)[C:7]([CH3:10])([CH3:9])[CH3:8])(=O)[CH3:2].C([O-])(=O)C.[NH4+:22]>C(O)(=O)C.O.[OH-].[Na+]>[CH3:8][C:7]([C:6]1[N:22]=[C:1]([CH3:2])[O:4][C:5]=1[C:12](=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:10])[CH3:9]

참가 물질

6

반응물 2

HCID 517165Ammonium AcetateHCID 104669154-(Acetyloxy)-2,2,6,6-tetramethyl 3,5-heptanedione

생성물 1

HCID 189253781-[4-(1,1-Dimethylethyl)-2-methyl-5-oxazolyl]-2,2-dimethyl-1-propanone수율 92.5%

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 962Water용매HCID 14798Sodium Hydroxide용매

실험 절차

A solution of 4-(acetyloxy)-2,2,6,6-tetramethyl 3,5-heptanedione (22 g, 0.09 mol) in acetic acid (100 mL) is treated with ammonium acetate (44 g). The reaction mixture is heated at reflux overnight. The reaction mixture is diluted with water and neutralized (to pH 5) by the addition of aqueous sodium hydroxide. The product is extracted into ethyl acetate (3×150 mL) and the combined organic layers are washed with 0.1 N NaOH, water, and then brine. The organic layer is dried and evaporated. The residue is taken up in hexane (50 mL) and applied to a pad of silica gel (500 g). The silica pad is eluted with hexane (100 mL). Then the product is eluted from the silica with hexane/ethyl acetate (4:1) to give 18.6 g (91%) of 1-[4-(1,1-dimethylethyl)-2-methyl-5-oxazolyl]-2,2-dimethyl-1-propanone as an oil. 1H-NMR (CDCl3) δ 2.60 (s, 3H, 2-Me), 1.35 (s, 9H, tbu), 1.31 (s, 9H, tbu). 13C--NMR (CDCl3) δ 195.8, 159.3, 157.6, 143.6, 44.2, 32.7, 28.4, 26.6.

후처리

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux overnight
  3. extractionThe product is extracted into ethyl acetate (3×150 mL)
  4. washthe combined organic layers are washed with 0.1 N NaOH, water
  5. customThe organic layer is dried
  6. customevaporated
  7. washThe silica pad is eluted with hexane (100 mL)
  8. washThen the product is eluted from the silica with hexane/ethyl acetate (4:1)

출처 및 근거

ORD 기록
ord-423d54bce0b9404dac5413ebf7e7ac6a
출처 데이터셋
uspto-grants-1995_07
특허 번호
US05432181

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