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

HRID 1899786노트

반응식

HRID 1899786 반응식
[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]

참가 물질

5

반응물 2

HCID 11219857methyl (E)-2-bromomethyl-beta-methoxycinnamateHCID 178517449HCID 178517449, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 178418647HCID 178418647, 화합물촉매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-72b3fd4572554d908acd68295613adb9
출처 데이터셋
uspto-grants-1996_11
특허 번호
US05573999

반응 노트

불러오는 중…