Diethyl Ether → 6-Methoxy-1,1,4,7-tetramethyl-1,2-dihydronaphthalene

HRID 1795578ノート

反応式

HRID 1795578 の反応式
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([CH3:15])([CH3:14])[CH2:8][CH2:9][C:10]2=O)=[CH:5][C:4]=1[CH3:16].C[Mg+].[Br-].[CH2:20](OCC)C>O1CCCC1>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6](=[CH:5][C:4]=1[CH3:16])[C:7]([CH3:15])([CH3:14])[CH2:8][CH:9]=[C:10]2[CH3:20]

参加物

5

反応物 3

HCID 3283Diethyl EtherHCID 12088903HCID 12088903、化合物2 回HCID 178418689HCID 178418689、化合物

生成物 1

HCID 222182896-Methoxy-1,1,4,7-tetramethyl-1,2-dihydronaphthalene収率 84.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

General Procedure A CeCl3 7 H2O (1.28 g, 3.4 mmol) was heated in an oil bath to 140-150° C. under high vacuum without stirring for 2 h, and then with stirring for 2 h. Argon was then introduced, and the flask was cooled to room temperature. Tetrahydrofuran (10 mL) was added, and the resulting slurry solution was stirred at room temperature under the argon atmosphere for 3 h. A solution of 7-methoxy-4,4,6-trimethyl-3,4-dihydro-2H-naphthalen-1-one (Compound 6, 0.53 g, 2.3 mmol) and 5 mL of tetrahydrofuran was added, and the reaction mixture was stirred for 1 h, then cooled to 0° C. A solution of 3 M MeMgBr in diethyl ether (1.2 mL, 3.4 mmol) was added, and the ice bath was removed. After 1 h, the reaction was poured into concentrated sulfuric acid in ice, extracted with ethyl acetate, washed with IN NaHCO3, brine, dried over MgSO4, and filtered. The solvent was removed to give 0.42 g (80%) of the title compound as an orange oil.

後処理

  1. stirringwith stirring for 2 h
  2. additionArgon was then introduced
  3. stirringthe resulting slurry solution was stirred at room temperature under the argon atmosphere for 3 h
  4. stirringthe reaction mixture was stirred for 1 h
  5. temperaturecooled to 0° C
  6. customthe ice bath was removed
  7. waitAfter 1 h
  8. additionthe reaction was poured into concentrated sulfuric acid in ice
  9. extractionextracted with ethyl acetate
  10. washwashed with IN NaHCO3, brine
  11. dry with materialdried over MgSO4
  12. filtrationfiltered
  13. customThe solvent was removed

出典と根拠

ORDレコード
ord-cb14d780aade44b38cc4ceedc71cf8eb
出典データセット
uspto-grants-2006_04
特許番号
US07026487B2

反応ノート

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