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

HRID 230828노트

반응식

HRID 230828 반응식
[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.[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]

참가 물질

5

반응물 3

HCID 8028Tetrahydrofuran2회HCID 21226445Aluminium lithium hydrideHCID 577634414-{1-ethyl-1-[4-(2-hydroxy-3,3-dimethyl-butoxy)-3-methyl-phenyl]-propyl}-N-methoxy-2,N-dimethyl-benzamide

생성물 1

HCID 577634244-{1-Ethyl-1-[4-(2-hydroxy-3,3-dimethyl-butoxy)-3-methyl-phenyl]-propyl}-2-methyl-benzaldehyde수율 73%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

To a mixture of enantiomer 2 of 4-{1-ethyl-1-[4-(2-hydroxy-3,3-dimethyl-butoxy)-3-methyl-phenyl]-propyl}-N-methoxy-2,N-dimethyl-benzamide (0.76 g, 1.75 mmol) and THF (20 mL) is added 1M LAH in THF (1.75 mL, 1.75 mmol) with cooling, 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 (0.48 g, 1.21 mmol, 73%).

후처리

  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

출처 및 근거

ORD 기록
ord-823ed6e125ae48289902158665b2f8ef
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07566803B2

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