Tetrahydrofuran → 6-Methoxy-10-(4-methoxy-phenyl)-9-methyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene

HRID 418948ノート

反応式

HRID 418948 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][CH:16]=1)[CH:13]([CH2:17]OS(C1C=CC(C)=CC=1)(=O)=O)[CH:12]([C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1)[CH:11]1[CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][CH:16]=1)[CH:13]([CH3:17])[CH:12]([C:29]1[CH:30]=[CH:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=1)[CH:11]1[CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]1

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 9357Potassium Sodium TartrateHCID 21226445Aluminium lithium hydrideHCID 72309434Toluene-4-sulfonic acid 6-methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-ylmethyl ester

生成物 1

HCID 666519736-Methoxy-10-(4-methoxy-phenyl)-9-methyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene収率 85.3%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

Combine toluene-4-sulfonic acid 6-methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-ylmethyl ester (0.471 g, 0.93 mmol), lithium aluminum hydride (0.069 g, 1.86 mmol), and tetrahydrofuran (8.0 mL), and reflux under nitrogen atmosphere. After 5 hours, quench reaction by adding reaction to a stirred solution of Rochelle's salt (Na K Tartrate) and ethyl acetate. After several hours, separate the organic phase and wash with brine. Dry the organic phase with anhydrous sodium sulfate and flash chromatograph using 0% to 20% ethyl acetate/hexanes to yield the titled compound (0.267 g, 85%) as a white solid. TLC Rf=0.43 in 3:1 hexanes:ethyl acetate. 1H NMR (CDCl3): 7.35 (d, 1H, J=8.4 Hz), 7.23 (d, 2H, J=8.4 Hz), 6.94 (m, 3H), 6.82 (dd, 1H, J=8.8, 2.6 Hz), 3.86 (s, 6H), 3.31 (m, 2H), 2.82 (dd, 1H, J=11.9, 2.6 Hz), 2.50 (d, 1H, J=13.7 Hz), 1.89 (m, 1H), 1.64 (m, 2H), 1.44 (m, 2H), 1.16 (m, 6H).

後処理

  1. customquench
  2. customreaction
  3. additionby adding
  4. waitAfter several hours
  5. customseparate the organic phase
  6. washwash with brine
  7. dry with materialDry the organic phase with anhydrous sodium sulfate and flash chromatograph

出典と根拠

ORDレコード
ord-b4e5c1b6e28947bf914efff539673bc8
出典データセット
uspto-grants-2012_01
特許番号
US08093302B2

反応ノート

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