Tetrahydrofuran → 4-{1-Ethyl-1-[4-(2-hydroxy-3,3-dimethyl-butoxy)-3-methyl-phenyl]-propyl}-2-methyl-benzaldehyde

HRID 502072ノート

反応式

HRID 502072 の反応式
[CH2:1]([C:3]([C:21]1[CH:32]=[CH:31][C:24]([C:25](N(OC)C)=[O:26])=[C:23]([CH3:33])[CH:22]=1)([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH:14]([OH:19])[C:15]([CH3:18])([CH3:17])[CH3:16])=[C:8]([CH3:20])[CH:7]=1)[CH2:4][CH3:5])[CH3:2].C1COCC1.C1COCC1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC>[CH2:1]([C:3]([C:21]1[CH:32]=[CH:31][C:24]([CH:25]=[O:26])=[C:23]([CH3:33])[CH:22]=1)([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH:14]([OH:19])[C:15]([CH3:17])([CH3:18])[CH3:16])=[C:8]([CH3:20])[CH:7]=1)[CH2:4][CH3:5])[CH3:2]

参加物

5

反応物 3

HCID 8028Tetrahydrofuran2 回HCID 577634414-{1-ethyl-1-[4-(2-hydroxy-3,3-dimethyl-butoxy)-3-methyl-phenyl]-propyl}-N-methoxy-2,N-dimethyl-benzamideHCID 68718528lithium aluminium hydride THF

生成物 1

HCID 577634244-{1-Ethyl-1-[4-(2-hydroxy-3,3-dimethyl-butoxy)-3-methyl-phenyl]-propyl}-2-methyl-benzaldehyde収率 67%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

To a mixture of enantiomer 1 of 4-{1-ethyl-1-[4-(2-hydroxy-3,3-dimethyl-butoxy)-3-methyl-phenyl]-propyl}-N-methoxy-2,N-dimethyl-benzamide (1.0 g, 2.42 mmol) and THF (10 mL) is added 1M in THF LAH (2.5 mL, 2.55 mmol) with cooling. THF (5 mL) was added and the solution stirred for 1 hour. The solution is diluted with Et2O (100 mL) and washed with 1M HCl (50 mL). The aqueous phase is extracted with Et2O (50 mL). The combined organic layers are washed with 1M HCl (50 mL), brine (50 mL), dried over MgSO4, filtered and concentrated to furnish the title compound (0.64 g, 1.61 mmol, 67%).

後処理

  1. temperaturewith cooling
  2. washwashed with 1M HCl (50 mL)
  3. extractionThe aqueous phase is extracted with Et2O (50 mL)
  4. washThe combined organic layers are washed with 1M HCl (50 mL), brine (50 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-bfbf07902e1d4c7b86af24b973b8d954
出典データセット
uspto-grants-2010_08
特許番号
US07772425B2

反応ノート

読み込み中…