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

HRID 1375632

反応式

HRID 1375632 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒2 回HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-85ee4dd0ad78463d8ae1db24a55b2f05
出典データセット
uspto-grants-2007_01
特許番号
US07169798B2

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