Methanesulfonic Acid → 5,6-Dimethoxy-3-phenyl-3,4-dihydronaphthalen-1(2H)-one

HRID 54121

反応式

HRID 54121 の反応式
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:11][CH:12]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:13][C:14](O)=[O:15].CS(O)(=O)=O>FC(F)(F)C(O)=O>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[C:5]2[C:4]=1[CH2:11][CH:12]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:13][C:14]2=[O:15]

参加物

4

反応物 2

HCID 6395Methanesulfonic AcidHCID 124785434-(2',3'-Dimethoxyphenyl) 3-phenylbutyric acid

生成物 1

HCID 124785445,6-Dimethoxy-3-phenyl-3,4-dihydronaphthalen-1(2H)-one収率 77%

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

実験手順

4-(2',3'-Dimethoxyphenyl)-3-phenylbutyric acid (13.3 g, 44.3 mmol), from Step 4, was treated with 14 mL (216 mmol) of methanesulfonic acid and 200 mL of trifluoroacetic acid at 60° C. for 1.5 h. After cooling the reaction mixture, the trifluoroacetic acid was removed in vacuo and ice water was added to the residue. Methylene chloride was added and the layers were separated. The organic layer was washed with 1N aqueous sodium hydroxide solution, water and brine, dried over anhydrous magnesium sulfate, filtered and Concentrated under reduced pressure. The residue was recrystallized three times from methanol to give 9.6 g (77% yield) of 5,6-dimethoxy-3-phenyl-1,2,3,4-tetrahydronaphthalen-1-one, m.p. 126°-128° C.; 1H NMR spectrum was identical to the spectrum reported for the product of Step 6 of Method A, Example 1.

後処理

  1. temperatureAfter cooling the reaction mixture
  2. customthe trifluoroacetic acid was removed in vacuo and ice water
  3. additionwas added to the residue
  4. additionMethylene chloride was added
  5. customthe layers were separated
  6. washThe organic layer was washed with 1N aqueous sodium hydroxide solution, water and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationConcentrated under reduced pressure
  10. customThe residue was recrystallized three times from methanol

出典と根拠

ORDレコード
ord-9a9cd6e9bf2540e69c43ebb5e2adea86
出典データセット
uspto-grants-1997_04
特許番号
US05621133

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