Allyl iodide → 2-allyl-2-butyl-6-methoxy-3,4-dihydro-1(2H)-naphthalenone

HRID 2113659

반응식

HRID 2113659 반응식
[H-].[Na+].[CH2:3]([CH:7]1[CH2:16][CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:17][CH3:18])[CH:13]=2)[C:8]1=[O:19])[CH2:4][CH2:5][CH3:6].[CH2:20](I)[CH:21]=[CH2:22]>CN(C=O)C>[CH2:22]([C:7]1([CH2:3][CH2:4][CH2:5][CH3:6])[CH2:16][CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:17][CH3:18])[CH:13]=2)[C:8]1=[O:19])[CH:21]=[CH2:20]

참가 물질

5

반응물 3

HCID 11166Allyl iodide2회HCID 24758Sodium hydrideHCID 586040732-butyl-6-methoxy-3,4-dihydro-1(2H)-naphthalenone

생성물 1

HCID 586040462-allyl-2-butyl-6-methoxy-3,4-dihydro-1(2H)-naphthalenone

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
2.5 °C

실험 절차

NaH (0.32 g of a 60% dispersion in mineral oil, 8.0 mmol) was added to an ice-cold solution of 2-butyl-6-methoxy-3,4-dihydro-1(2H)-naphthalenone (1.55 g, 6.7 mmol) in anhydrous DMF (30 mL). The mixture was purged with N2 and stirred at 0-5° C. for 45 minutes. Allyl iodide (0.91 mL, 10.0 mmol) was added and, after a few minutes, the cooling bath was removed and the mixture was stirred overnight at room temperature. Additional NaH (0.16 g of a 61.1% dispersion in mineral oil, 4.1 mmol) was added and the mixture was stirred at room temperature for 15 minutes. Allyl iodide (0.46 mL, 5.0 mmol) was added and the mixture was stirred at room temperature for 24 hours. The mixture was partitioned between EtOAc and water, and the aqueous phase was back-extracted with several portions of EtOAc. The combined organics were washed with brine, dried over MgSO4, filtered, and concentrated under vacuum. The residue was purified by Biotage™ (Charlottesville, Va.) flash chromatography on a 40M (4×15 cm) silica gel column, eluting with 1% to 4% EtOAc in hexane, to afford 2-allyl-2-butyl-6-methoxy-3,4-dihydro-1(2H)-naphthalenone as an oil.

후처리

  1. customThe mixture was purged with N2
  2. customthe cooling bath was removed
  3. stirringthe mixture was stirred overnight at room temperature
  4. additionAdditional NaH (0.16 g of a 61.1% dispersion in mineral oil, 4.1 mmol) was added
  5. stirringthe mixture was stirred at room temperature for 15 minutes
  6. stirringthe mixture was stirred at room temperature for 24 hours
  7. customThe mixture was partitioned between EtOAc and water
  8. extractionthe aqueous phase was back-extracted with several portions of EtOAc
  9. washThe combined organics were washed with brine
  10. dry with materialdried over MgSO4
  11. filtrationfiltered
  12. concentrationconcentrated under vacuum
  13. customThe residue was purified by Biotage™ (Charlottesville, Va.) flash chromatography on a 40M (4×15 cm) silica gel column
  14. washeluting with 1% to 4% EtOAc in hexane

출처 및 근거

ORD 기록
ord-4ffa97b3f8e743c692bc0288aacb38db
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07432284B2

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