Citric Acid → 4-(5-Bromopentyl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-5-one

HRID 466961

反応式

HRID 466961 の反応式
[O:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[C:5](=[O:12])[NH:4][CH2:3][CH2:2]1.[Br:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]Br.[H-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C)C=O>[Br:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][N:4]1[C:5](=[O:12])[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[O:1][CH2:2][CH2:3]1

参加物

6

反応物 4

HCID 311Citric AcidHCID 81001,5-DibromopentaneHCID 24758Sodium hydrideHCID 3406292,3,4,5-Tetrahydro-1,4-benzoxazepin-5-one

生成物 1

HCID 198130564-(5-Bromopentyl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-5-one収率 65%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

In 20 ml of dimethylformamide (DMF) was dissolved 100 mg of 2,3,4,5-tetrahydro-1,4-benzoxazepin-5-one, and the solution then ice-cooled. Then, to the resulting solution were added 0.251 ml (3 equivalents) of 1,5-dibromopentane and 29.4 mg (1.2 equivalent) of a 60% sodium hydride oil dispersion, and the mixture was stirred for one hour with ice-cooling. The reaction solution was poured into a citric acid aqueous solution and extracted with ethyl acetate, and the ethyl acetate phase was washed with an aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and then filtered. The filtrate was then concentrated and the resulting residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (8:2)) to give 124 mg (yield: 65.0%) of the title compound.

後処理

  1. temperaturethe solution then ice-cooled
  2. temperaturecooling
  3. extractionextracted with ethyl acetate
  4. washthe ethyl acetate phase was washed with an aqueous saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was then concentrated
  8. customthe resulting residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (8:2))

出典と根拠

ORDレコード
ord-5a307d9441d2491899e5958bbc821fa0
出典データセット
uspto-grants-1992_10
特許番号
US05158947

関連ノート

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