Methyl acetoacetate → Methyl 5-methyl-3-phenyl-1,2-oxazole-4-carboxylate

HRID 2120855노트

반응식

HRID 2120855 반응식
[C:1](=[N:9][OH:10])(Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:11]([O:17][CH3:18])(=[O:16])[CH2:12][C:13]([CH3:15])=O.C(N(CC)CC)C.C(OCC)(=O)C>C(O)C.C(Cl)Cl>[CH3:18][O:17][C:11]([C:12]1[C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[N:9][O:10][C:13]=1[CH3:15])=[O:16]

참가 물질

7

반응물 4

HCID 7757Methyl acetoacetateHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 2756315N-hydroxybenzenecarboximidoyl chloride

생성물 1

HCID 727920Methyl 5-methyl-3-phenyl-1,2-oxazole-4-carboxylate수율 39%

시약·촉매·용매 2

HCID 702Ethanol용매2회HCID 6344Dichloromethane용매

실험 절차

An ethanol solution of freshly prepared benzoyl chloride oxime (14.0 g, 90 mmol) (100 mL) was added dropwise, at 5° C. to methyl acetoacetate (11.18 g, 96 mmol) and triethyl amine (13 mL, 103 mmol) in ethanol (50 ml). After stirring for 12 hr at ambient temperature, the solution was diluted with CH2Cl2, washed with 1N HCl. saturated NaHCO3, brine, dried over MgSO4 and evaporated to give amber oil. Flash chromatography (silica) with 10% ethyl acetate in hexanes afforded the title compound (7.56 g, 39% yield) as a white solid: MS m/z MH+218 (100); 1H NMR (CDCl3) δ 2.78 (s, 3H), 3.81 (s, 3H), 7.45-7.55 (m, 3H), 7.65-7.69 (m, 2H).

후처리

  1. washwashed with 1N HCl
  2. dry with materialsaturated NaHCO3, brine, dried over MgSO4
  3. customevaporated
  4. customto give amber oil

출처 및 근거

ORD 기록
ord-0c9ed052a79845ebb3fc2724cf6a8f4f
출처 데이터셋
uspto-grants-2004_02
특허 번호
US06693108B2

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