Sodium Hydroxide → HCID 19961233, 화합물

HRID 233386노트

반응식

HRID 233386 반응식
[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

참가 물질

9

반응물 4

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

생성물 1

HCID 19961233HCID 19961233, 화합물수율 73.4%

시약·촉매·용매 4

HCID 6451240Aluminum(III) Chloride촉매HCID 962Water용매2회HCID 3283Diethyl Ether용매HCID 6342Acetonitrile용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-4402ab665a964550bb7fa0dfde3069a1
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05591884

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