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 253152노트

반응식

HRID 253152 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

반응 조건

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-38afeb4e81324e23b8865bdfcdab89e6
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07872009B2

반응 노트

불러오는 중…