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 253152ノート

反応式

HRID 253152 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-38afeb4e81324e23b8865bdfcdab89e6
出典データセット
uspto-grants-2011_01
特許番号
US07872009B2

反応ノート

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