Water → 4-Phenylbicyclo[2.2.2]octane-1-carboxaldehyde

HRID 908111노트

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HRID 908111 반응식
CON(C)[C:4]([C:6]12[CH2:13][CH2:12][C:9]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)([CH2:10][CH2:11]1)[CH2:8][CH2:7]2)=[O:5].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.CCOC(C)=O>C1COCC1>[C:14]1([C:9]23[CH2:12][CH2:13][C:6]([CH:4]=[O:5])([CH2:11][CH2:10]2)[CH2:7][CH2:8]3)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 59379799N-methoxy-N-methyl-1-phenylbicyclo[2.2.2]octane-4-carboxamide2회

생성물 1

HCID 593797914-Phenylbicyclo[2.2.2]octane-1-carboxaldehyde

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

To an ice water cooled solution of N-methoxy-N-methyl-1-phenylbicyclo[2.2.2]octane-4-carboxamide (Intermediate 5; 8.49 g, 31.05 mmol) in anhydrous THF (100 mL) under nitrogen was added lithium aluminium hydride (1M solution in THF, 62 mL) dropwise and the reaction mixture was allowed to stir at 0° C. for 1 hr. Water (25 mL) was added cautiously followed by EtOAc (˜100 mL) and the mixture was filtered through a pad of celite washing with EtOAc (50 mL). The filtrate was washed with brine (150 mL), the organic phase separated, dried (MgSO4) and concentrated to leave the title compound as a colourless oil which formed a solid on standing (6.92 g, 32.28 mmol, 100%); 1H NMR (CDCl3) δ 1.72-1.83 (6H, m), 1.87-1.94 (6H, m), 7.17-7.22 (1H, m), 7.31-7.33 (4H, m), 9.53 (1H, s); GC-MS EI m/e M+ 214.

후처리

  1. filtrationthe mixture was filtered through a pad of celite
  2. washwashing with EtOAc (50 mL)
  3. washThe filtrate was washed with brine (150 mL)
  4. customthe organic phase separated
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-d7556b3d72374c619cfc6200c1c2fdf3
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08017603B2

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