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

HRID 2177862ノート

反応式

HRID 2177862 の反応式
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

参加物

7

反応物 4

HCID 1118Sulfuric AcidHCID 24083Sulfuric acid magnesium salt (1:1)HCID 516892Sodium BicarbonateHCID 671080273-(Furan-3-yl)-2-methoxy-6-(phenylthiomethyl)benzoic acid2 回

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒3 回HCID 6386tert-Butanol溶媒

実験手順

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.

後処理

  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%

出典と根拠

ORDレコード
ord-e5858a4945d94139aa33aae9a02e484e
出典データセット
uspto-grants-2015_06
特許番号
US09067905B2

反応ノート

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