methyl (E)-2-bromomethyl-beta-methoxycinnamate → methyl (E)-beta-methoxy-2-(4-phenyl-2-thiazolyloxymethyl)cinnamate

HRID 1899786ノート

反応式

HRID 1899786 の反応式
[OH:1][C:2]1[S:3][CH:4]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1.[CH3:13][O:14]/[C:15](/[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:27]Br)=[CH:16]/[C:17]([O:19][CH3:20])=[O:18]>CN(C=O)C.C(=O)([O-])[O-].[Ag+2]>[CH3:13][O:14]/[C:15](/[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:27][O:1][C:2]1[S:3][CH:4]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1)=[CH:16]/[C:17]([O:19][CH3:20])=[O:18]

参加物

5

反応物 2

HCID 11219857methyl (E)-2-bromomethyl-beta-methoxycinnamateHCID 178517449HCID 178517449、化合物

生成物 1

HCID 86749648methyl (E)-beta-methoxy-2-(4-phenyl-2-thiazolyloxymethyl)cinnamate収率 56.2%

試薬・触媒・溶媒 2

HCID 178418647HCID 178418647、化合物触媒HCID 6228Dimethylformamide溶媒

実験手順

1.2 g (0.007 mol) of 2-hydroxy-4-phenylthiazole, 2.1 g (0.0077 mol) of silver carbonate and 2.1 g (0.0074 mol) of methyl (E)-β-methoxy-2-bromomethylcinnamate (see Example 2) are stirred in 15 ml of DMF at 60° C. for 8 hours. The precipitate is filtered off and the DMF solution is poured into 100 ml of water, and the mixture is extracted with methyl tert-butyl ether. Drying and concentration of the organic phase result in a brown oil which is chromatographed on silica gel with cyclohexane/acetone (95:5). 1.5 g (56% yield) of methyl (E)-β-methoxy-2-(4-phenyl-2-thiazolyloxymethyl)cinnamate as yellowish oil are isolated as the main fraction.

後処理

  1. filtrationThe precipitate is filtered off
  2. additionthe DMF solution is poured into 100 ml of water
  3. extractionthe mixture is extracted with methyl tert-butyl ether
  4. customDrying
  5. customconcentration of the organic phase result in a brown oil which
  6. customis chromatographed on silica gel with cyclohexane/acetone (95:5)

出典と根拠

ORDレコード
ord-72b3fd4572554d908acd68295613adb9
出典データセット
uspto-grants-1996_11
特許番号
US05573999

反応ノート

読み込み中…