Hydrochloric Acid → 3-[4-(3-Benzyloxy-5-methyl-phenoxy)-2-methyl-phenyl]-acrylic acid ethyl ester

HRID 1822283

반응식

HRID 1822283 반응식
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([OH:16])[CH:12]=[C:13]([CH3:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:17]([O:19][C:20](=[O:31])[CH:21]=[CH:22][C:23]1[CH:28]=[CH:27][C:26](F)=[CH:25][C:24]=1[CH3:30])[CH3:18].C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O.CCOCC>[CH2:17]([O:19][C:20](=[O:31])[CH:21]=[CH:22][C:23]1[CH:28]=[CH:27][C:26]([O:16][C:11]2[CH:12]=[C:13]([CH3:15])[CH:14]=[C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:10]=2)=[CH:25][C:24]=1[CH3:30])[CH3:18]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 109983793-(Benzyloxy)-5-methylphenolHCID 537177243-(4-Fluoro-2-methyl-phenyl)-acrylic acid ethyl ester

생성물 1

HCID 690796773-[4-(3-Benzyloxy-5-methyl-phenoxy)-2-methyl-phenyl]-acrylic acid ethyl ester수율 58.6%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 3283Diethyl Ether용매

반응 조건

온도
130 °C

실험 절차

A mixture of 3-benzyloxy-5-methyl-phenol (3.24 g, 15.1 mmol), 3-(4-fluoro-2-methyl-phenyl)-acrylic acid ethyl ester (3.15 g, 15.1 mmol) and 325 mesh potassium carbonate (2.51 g, 18.2 mmol) in dry DMSO (40 mL) is heated to 130° C. and stirred for 20 hours under N2. The reaction is cooled and acidified with 1 N HCl (30 mL). The mixture is then diluted with Et2O and extracted with water. The organic layer is dried (Na2SO4), and the solvent is removed in vacuo to afford crude product that is absorbed on silica gel and purified by flash chromatography using 9/1 hexanes/ethyl acetate to afford 3.56 g (58%) of the title compound. Rf=0.39 (4/1 hexanes/EtOAc). 1H NMR (400 MHz, CDCl3); MS (ES+) m/z mass calculated for C26H26O4 402, found 403 (M+1, 100%).

후처리

  1. temperatureThe reaction is cooled
  2. extractionextracted with water
  3. dry with materialThe organic layer is dried (Na2SO4)
  4. customthe solvent is removed in vacuo
  5. customto afford crude product that
  6. customis absorbed on silica gel
  7. custompurified by flash chromatography

출처 및 근거

ORD 기록
ord-f68ddca77c1d4435a48459c8f2bbe4d8
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07608639B2

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