Sodium Hydroxide → HCID 19961233、化合物

HRID 1089008ノート

反応式

HRID 1089008 の反応式
[CH3:1][O:2][C:3]1[C:12]([O:13][CH3:14])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH:6]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:7][C:8]2=[O:15].C[Si]([C:26]#[N:27])(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>C(OCC)C.[Cl-].[Al+3].[Cl-].[Cl-].O.C(#N)C>[NH2:27][CH2:26][C:8]1([OH:15])[C:9]2[C:4](=[C:3]([O:2][CH3:1])[C:12]([O:13][CH3:14])=[CH:11][CH:10]=2)[CH2:5][CH:6]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:7]1

参加物

9

反応物 4

HCID 14798Sodium HydroxideHCID 82115Trimethylsilyl cyanideHCID 124785445,6-Dimethoxy-3-phenyl-3,4-dihydronaphthalen-1(2H)-oneHCID 21226445Aluminium lithium hydride

生成物 1

HCID 19961233HCID 19961233、化合物収率 73.4%

試薬・触媒・溶媒 4

HCID 6451240Aluminum(III) Chloride触媒HCID 962Water溶媒2 回HCID 3283Diethyl Ether溶媒HCID 6342Acetonitrile溶媒

実験手順

5,6-Dimethoxy-3-phenyl-1,2,3,4-tetrahydro-1-naphthalenone (14.6 g, 51.7 mmol), from Example 1, 24 mL of acetonitrile, 10.3 g (104 mmol) of trimethylsilylcyanide, commercially available from Aldrich Chemical Company, and 100 mg of aluminum chloride were mixed together and heated at reflux temperature for 2.5 h. The reaction mixture was cooled and concentrated. The residue was dissolved in diethyl ether and added dropwise to a solution of 4.3 g (113 mmol) of lithium aluminum hydride in 101 mL of diethyl ether. After the reaction mixture was heated at reflux temperature for 2.5 h, 4.3 mL of water was added dropwise, followed by 4.3 mL of 15% aqueous sodium hydroxide solution, followed by 13 mL of water. The reaction mixture was stirred until a qranular precipitate formed. The solid was filtered and washed with 3×80 mL of methylene chloride. The filtrate was concentrated and the resultant solid was triturated with ethyl acetate/hexane to give 11.9 g (73% yield) of the title compound, m.p. 175°-176° C. 1H NMR (d6DMSO) delta 2.03 (t, 1H), 2.28 (dt, 1H), 2.65 (dd, 1H), 2.83 (dd, 1H), 2.95-3.1 (m, 2H), 3.28 (dd, 1H), 3.75 (s, 3H), 3.86 (s, 3H), 6.87 (d, 1H), 7.2-7.4 (m, 6H)

後処理

  1. temperatureheated
  2. temperatureat reflux temperature for 2.5 h
  3. temperatureThe reaction mixture was cooled
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in diethyl ether
  6. temperatureAfter the reaction mixture was heated
  7. temperatureat reflux temperature for 2.5 h
  8. customformed
  9. filtrationThe solid was filtered
  10. washwashed with 3×80 mL of methylene chloride
  11. concentrationThe filtrate was concentrated
  12. customthe resultant solid was triturated with ethyl acetate/hexane

出典と根拠

ORDレコード
ord-3c38cd36116146c0b04b3a743872b920
出典データセット
uspto-grants-1990_10
特許番号
US04963568

反応ノート

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