Hydrochloric Acid → 3-{4-[3-(5,5-Dimethyl-3-trifluoromethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-3-oxo-propenyl]-2-ethyl-6-methyl-phenyl}-acrylic acid ethyl ester

HRID 1665957노트

반응식

HRID 1665957 반응식
[CH3:1][C:2]1([CH3:18])[CH2:17][CH2:16][C:5]2=[C:6]([C:13](=[O:15])[CH3:14])[S:7][C:8]([C:9]([F:12])([F:11])[F:10])=[C:4]2[CH2:3]1.[CH2:19]([C:21]1[CH:26]=[C:25]([CH:27]=O)[CH:24]=[C:23]([CH3:29])[C:22]=1[CH:30]=[CH:31][C:32]([OH:34])=[O:33])[CH3:20].Cl.[CH2:36](O)[CH3:37]>C(O)(C)C.C([O-])(O)=O.[Na+]>[CH2:36]([O:34][C:32](=[O:33])[CH:31]=[CH:30][C:22]1[C:23]([CH3:29])=[CH:24][C:25]([CH:27]=[CH:14][C:13]([C:6]2[S:7][C:8]([C:9]([F:12])([F:10])[F:11])=[C:4]3[CH2:3][C:2]([CH3:18])([CH3:1])[CH2:17][CH2:16][C:5]=23)=[O:15])=[CH:26][C:21]=1[CH2:19][CH3:20])[CH3:37]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 575089061-(5,5-Dimethyl-3-trifluoromethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-ethanoneHCID 765393093-(2-Ethyl-4-formyl-6-methyl-phenyl)-acrylic acid

생성물 1

HCID 671883473-{4-[3-(5,5-Dimethyl-3-trifluoromethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-3-oxo-propenyl]-2-ethyl-6-methyl-phenyl}-acrylic acid ethyl ester

시약·촉매·용매 2

HCID 3776Isopropanol용매HCID 516892Sodium Bicarbonate용매

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온도
65 °C

실험 절차

A solution of 1-(5,5-dimethyl-3-trifluoromethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-ethanone (500 mg, 1.81 mmol) and 3-(2-ethyl-4-formyl-6-methyl-phenyl)-acrylic acid (395 mg, 1.81 mmol) in ethanol (25 mL) is treated with 5 N HCl in isopropanol (15 mL). The orange brown reaction mixture is stirred at 65° C. for 64 h. The mixture is diluted with sat. aq. NaHCO3 solution and extracted twice with EA. The organic extracts are washed with sat. NaHCO3 solution, dried over MgSO4, filtered and the solvent of the filtrate is evaporated. The crude product is purified by CC on silica gel eluting with heptane:EA 9:1 to give 3-{4-[3-(5,5-dimethyl-3-trifluoromethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-3-oxo-propenyl]-2-ethyl-6-methyl-phenyl}-acrylic acid ethyl ester (634 mg, contains traces of the corresponding isopropyl ester) as a colourless oil; LC-MS: tR=1.32 min, [M+1]=505.04.

후처리

  1. extractionextracted twice with EA
  2. washThe organic extracts are washed with sat. NaHCO3 solution
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvent of the filtrate is evaporated
  6. customThe crude product is purified by CC on silica gel eluting with heptane:EA 9:1

출처 및 근거

ORD 기록
ord-7fc677ff6c9247cab480c0dfed2b6fc3
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08039644B2

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