Bromocyclopropane → 4-Cyclopropyl-3,4-dihydro-2H-benzo[1,4]oxazine

HRID 72560

反応式

HRID 72560 の反応式
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[NH:4][CH2:3][CH2:2]1.[CH3:11][C:12]([CH3:15])([O-])C.[K+].BrC1CC1>CN(C=O)C>[CH:15]1([N:4]2[C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[O:1][CH2:2][CH2:3]2)[CH2:12][CH2:11]1

参加物

5

反応物 3

HCID 78037BromocyclopropaneHCID 5850963,4-Dihydro-2H-1,4-benzoxazineHCID 23665647Potassium tert-butoxide

生成物 1

HCID 583408104-Cyclopropyl-3,4-dihydro-2H-benzo[1,4]oxazine収率 68.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a stirred solution of 3,4-dihydro-2H-benzo[1,4]oxazine (5 g, 37.0 mmol) in DMF (20 mL) was added potassium tert-butoxide (6.22 g, 55.55 mmol) at 0° C. After stirring for 5 min, bromo-cyclopropane (4.44 mL, 55.55 mmol) was added and the reaction mixture was stirred for another 4 h at room temperature. The reaction was quenched by addition of water and extracted with ethyl acetate (50×2 mL). The organic layer was washed with water (20 mL), concentrated and purified by silica gel column chromatography to furnish 4-Cyclopropyl-3,4-dihydro-2H-benzo[1,4]oxazine (4.42 g).

後処理

  1. stirringthe reaction mixture was stirred for another 4 h at room temperature
  2. customThe reaction was quenched by addition of water
  3. extractionextracted with ethyl acetate (50×2 mL)
  4. washThe organic layer was washed with water (20 mL)
  5. concentrationconcentrated
  6. custompurified by silica gel column chromatography

出典と根拠

ORDレコード
ord-171553ac0f9f49ccadb845cb054be1ea
出典データセット
uspto-grants-2014_09
特許番号
US08828951B2

関連ノート

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