Hydroxyamine hydrochloride → Methyl 4-{3-[4-(pentyloxy)phenyl]-1,2-oxazol-5-YL}benzoate

HRID 1386618ノート

反応式

HRID 1386618 の反応式
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[CH:12][C:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:17][CH:16]=2)=O)=[CH:7][CH:6]=1)=[O:4].Cl.[OH:28][NH2:29]>C(O)C.C(OCC)(=O)C.ClCCCl.[O-2].[Mn+4].[O-2]>[CH2:22]([O:21][C:18]1[CH:19]=[CH:20][C:15]([C:13]2[CH:12]=[C:11]([C:8]3[CH:9]=[CH:10][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=3)[O:28][N:29]=2)=[CH:16][CH:17]=1)[CH2:23][CH2:24][CH2:25][CH3:26]

参加物

7

反応物 2

HCID 443297Hydroxyamine hydrochlorideHCID 541783721-(4-Methoxycarbonylphenyl)-3-(4-n-pentyloxyphenyl)-1-propene-3-one

生成物 1

HCID 21182499Methyl 4-{3-[4-(pentyloxy)phenyl]-1,2-oxazol-5-YL}benzoate収率 23.6%

試薬・触媒・溶媒 4

HCID 178418406HCID 178418406、化合物触媒HCID 111,2-Dichloroethane溶媒HCID 702Ethanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 1-(4-Methoxycarbonylphenyl)-3-(4-n-pentyloxyphenyl)-1-propen-3-one (4.0 g) and hydroxyamine hydrochloride (3.93 g) in ethanol (40 ml) was refluxed for 4 hours. The mixture was diluted with ethyl acetate, and the organic layer was washed with water (×2), brine and dried over magnesium sulfate. The solvents were removed under reduced pressure to give crude oxime. To a solution of crude oxime in 1,2-dichloroethane (20 ml) was added activated-manganese(IV) oxide (10.0 g). The reaction mixture was refluxed for 2 hours and filtered. The residue was washed with dichloromethane. The solvents were removed under reduced pressure and the residue was triturated with acetonitrile. The solid was collected by filtration and dried to give Methyl 4-[3-(4-n-pentyloxyphenyl)isoxazol-5-yl]benzoate (0.98 g).

後処理

  1. washthe organic layer was washed with water (×2), brine
  2. dry with materialdried over magnesium sulfate
  3. customThe solvents were removed under reduced pressure
  4. customto give crude oxime
  5. temperatureThe reaction mixture was refluxed for 2 hours
  6. filtrationfiltered
  7. washThe residue was washed with dichloromethane
  8. customThe solvents were removed under reduced pressure
  9. customthe residue was triturated with acetonitrile
  10. filtrationThe solid was collected by filtration
  11. customdried

出典と根拠

ORDレコード
ord-46ccb1d39d8547b9b724a41c8a6ec8b7
出典データセット
uspto-grants-2001_07
特許番号
US06265536B1

反応ノート

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