4-bromo-6-methoxy-2,2-dimethyl-3,4-dihydronaphthalen-1(2H)-one → 4-azido-6-methoxy-2,2-dimethyl-3,4-dihydronaphthalen-1(2H)-one

HRID 1696335노트

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HRID 1696335 반응식
Br[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5](=[O:14])[C:4]([CH3:16])([CH3:15])[CH2:3]1.[N:17]([Na])=[N+:18]=[N-:19]>CN(C=O)C>[N:17]([CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5](=[O:14])[C:4]([CH3:16])([CH3:15])[CH2:3]1)=[N+:18]=[N-:19]

참가 물질

4

반응물 2

HCID 668447194-bromo-6-methoxy-2,2-dimethyl-3,4-dihydronaphthalen-1(2H)-oneHCID 178514644HCID 178514644, 화합물

생성물 1

HCID 866140234-azido-6-methoxy-2,2-dimethyl-3,4-dihydronaphthalen-1(2H)-one수율 90%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

4-Bromo-6-methoxy-2,2-dimethyl-3,4-dihydronaphthalen-1(2H)-one (3.9 g, 14 mmol) was added to DMF (10 mL) followed by azidosodium (3.6 g, 55 mmol). The mixture was heated to 60° C. overnight. The reaction was cooled to RT and quenched with water (25 mL). The aqueous layer was extracted with Et2O (3×100 mL). The combined organic layers were washed with brine, dried over MgSO4 and filtered. The solvent was evaporated and the residue was purified by column chromatography (0-50% EtOAc/Hexane to provide the title compound as a white solid (3.05 g, 90% yield). MS m/z: 268.2 (M+Na).

후처리

  1. temperatureThe reaction was cooled to RT
  2. customquenched with water (25 mL)
  3. extractionThe aqueous layer was extracted with Et2O (3×100 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customThe solvent was evaporated
  8. customthe residue was purified by column chromatography (0-50% EtOAc/Hexane

출처 및 근거

ORD 기록
ord-24dbf30c4c494c088d2bcc6fba81703f
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163766B2

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