Ethyl Bromide → 1-ethyl-3-methyl-1,3,9,10,11,12-hexahydro-2H-quino[4,3,2-ef][1,4]benzoxazepin-2-one

HRID 981935ノート

反応式

HRID 981935 の反応式
[CH3:1][CH:2]1[C:8](=[O:9])[NH:7][C:6]2=[C:10]3[C:15](=[N:16][C:17]4=[CH:18][CH:19]=[CH:20][C:4](=[C:5]24)[O:3]1)[CH2:14][CH2:13][CH2:12][CH2:11]3.[CH3:21][C:22](C)([O-])C.[K+].BrCC>O1CCCC1>[CH2:21]([N:7]1[C:6]2=[C:10]3[C:15](=[N:16][C:17]4=[CH:18][CH:19]=[CH:20][C:4](=[C:5]24)[O:3][CH:2]([CH3:1])[C:8]1=[O:9])[CH2:14][CH2:13][CH2:12][CH2:11]3)[CH3:22]

参加物

5

反応物 3

HCID 6332Ethyl BromideHCID 23665647Potassium tert-butoxideHCID 541566201,3,9,10,11,12-Hexahydro-3-methyl-2H-quino[4,3,2-ef][1,4]benzoxazepin-2-one

生成物 1

HCID 543766401-ethyl-3-methyl-1,3,9,10,11,12-hexahydro-2H-quino[4,3,2-ef][1,4]benzoxazepin-2-one収率 85%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a suspension of 1,3,9,10,11,12-hexahydro-3-methyl-2H-quino[4,3,2-ef][1,4]benzoxazepin-2-one (4.82 g) in dry tetrahydrofuran (150 ml) was added potassium tert-butoxide (2.42 g), with stirring. After 20 mins, bromoethane (5.37 ml) was added, and the reaction mixture was refluxed overnight. The reaction mixture was concentrated, diluted with saturated potassium carbonate solution, and extracted with ethyl acetate. The organic extracts were dried over anhydrous magnesium sulfate, concentrated, and the residue was adhered to silica and flash chromatographed (30% ethyl acetate/hexane). The appropriate fractions were concentrated. Trituration of the residue with diethyl ether/pentane (1/1) gave 4.51 g (85%) of 1-ethyl-3-methyl-1,3,9,10,11,12-hexahydro-2H-quino[4,3,2-ef][1,4]benzoxazepin-2-one.

後処理

  1. temperaturethe reaction mixture was refluxed overnight
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with saturated potassium carbonate solution
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic extracts were dried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customchromatographed (30% ethyl acetate/hexane)
  8. concentrationThe appropriate fractions were concentrated

出典と根拠

ORDレコード
ord-abf97870a96846bab7aab8093681537b
出典データセット
uspto-grants-1991_02
特許番号
US04994452

反応ノート

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