Sulfuric Acid → t-Butyl 3-(furan-3-yl)-2-methoxy-6-(phenylthiomethyl)benzoate

HRID 2177862노트

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HRID 2177862 반응식
S(=O)(=O)(O)O.S([O-])([O-])(=O)=O.[Mg+2].[O:12]1[CH:16]=[CH:15][C:14]([C:17]2[C:18]([O:34][CH3:35])=[C:19]([C:23]([CH2:26][S:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:24][CH:25]=2)[C:20]([OH:22])=[O:21])=[CH:13]1.C(=O)([O-])O.[Na+]>C(Cl)Cl.C(O)(C)(C)C>[O:12]1[CH:16]=[CH:15][C:14]([C:17]2[C:18]([O:34][CH3:35])=[C:19]([C:23]([CH2:26][S:27][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)=[CH:24][CH:25]=2)[C:20]([O:22][C:14]([CH3:17])([CH3:15])[CH3:13])=[O:21])=[CH:13]1

참가 물질

7

반응물 4

HCID 1118Sulfuric AcidHCID 24083Sulfuric acid magnesium salt (1:1)HCID 516892Sodium BicarbonateHCID 671080273-(Furan-3-yl)-2-methoxy-6-(phenylthiomethyl)benzoic acid2회

생성물 1

HCID 67107958t-Butyl 3-(furan-3-yl)-2-methoxy-6-(phenylthiomethyl)benzoate수율 119.8%

시약·촉매·용매 2

HCID 6344Dichloromethane용매3회HCID 6386tert-Butanol용매

실험 절차

Concentrated sulphuric acid (0.31 g) was added to a stirred suspension of magnesium sulphate (1.31 g) in DCM (10 ml) in a sealed vial and the mixture was stirred for 5 minutes before addition of a solution of 3-(furan-3-yl)-2-methoxy-6-(phenylthiomethyl)benzoic acid (Intermediate 223, 0.96 g) in DCM (8 ml) and t-butanol (1.03 g). The mixture was stirred in a sealed tube for 48 hours. DCM and saturated aqueous sodium hydrogen carbonate were added to the mixture and the organic layer was separated, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-100%, to give t-butyl 3-(furan-3-yl)-2-methoxy-6-(phenylthiomethyl)benzoate (0.67 g) as a colourless gum.

후처리

  1. customthe organic layer was separated
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customThe filtrate was evaporated to dryness
  5. customthe residue was purified by chromatography on silica
  6. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-100%

출처 및 근거

ORD 기록
ord-e5858a4945d94139aa33aae9a02e484e
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09067905B2

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