Sodium Hydroxide → HCID 19961233、化合物

HRID 233386ノート

反応式

HRID 233386 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-tetrahydronaphthalen-1-one (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 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 a second 4.3 mL of water. The reaction mixture was stirred until a granular precipitate formed. The solid was filtered and washed with 30×80 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 (d6 -DMSO) δ: 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. temperatureAfter the reaction mixture was heated
  6. temperatureat reflux temperature for 2.5 h
  7. customformed
  8. filtrationThe solid was filtered
  9. washwashed with 30×80 mL of methylene chloride
  10. concentrationThe filtrate was concentrated
  11. customthe resultant solid was triturated with ethyl acetate/hexane

出典と根拠

ORDレコード
ord-4402ab665a964550bb7fa0dfde3069a1
出典データセット
uspto-grants-1997_01
特許番号
US05591884

反応ノート

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