Water → HCID 22064029、化合物

HRID 433908ノート

反応式

HRID 433908 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:4][C:3]=1[O:14][CH3:15].C([Li])CCC.C([O:23][CH2:24]C)C.[OH2:26]>O1CCCC1>[CH3:15][O:14][C:3]1[CH:4]=[C:5]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:6]=[CH:7][C:2]=1[C:24]([OH:23])=[O:26]

参加物

6

反応物 4

HCID 962WaterHCID 3283Diethyl EtherHCID 220640394-(4-Bromo-3-methoxyphenyl)morpholineHCID 178418339Butyllithium

生成物 1

HCID 22064029HCID 22064029、化合物収率 66%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To a stirred solution of 4-bromo-3-methoxy-1-morpholinobenzene (104 mg, 0.382 mmol) in anhydrous tetrahydrofuran (3 mL) at −78° C. was slowly added n-butyl lithium (1.3 M solution in hexanes, 325 μL, 0.420 mmol) under nitrogen. The cooling medium was exchanged with an ice-bath, and the mixture was stirred for 5 min. After cooling again to −78° C., carbon dioxide from evaporation of dry ice was bubbled through the solution for 10 min. A precipitate was formed, and the reaction mixture was allowed to reach room temperature. Diethyl ether and water were added. The mixture was extracted, the layers were separated, and the aqueous layer was acidified to pH 4. The dark blue aqueous solution was extracted several times with diethyl ether and ethyl acetate at pH 4 to pH 6. The combined organic layers were dried (MgSO4), and the solvent was removed in vacuo affording 60 mg (66% yield) of the title compound as a white solid: mp 158-160° C.; EIMS m/z (relative intensity) 237 (100, M+).

後処理

  1. customat −78° C.
  2. customThe cooling medium was exchanged with an ice-bath
  3. customcarbon dioxide from evaporation of dry ice
  4. customwas bubbled through the solution for 10 min
  5. customA precipitate was formed
  6. customto reach room temperature
  7. extractionThe mixture was extracted
  8. customthe layers were separated
  9. extractionThe dark blue aqueous solution was extracted several times with diethyl ether and ethyl acetate at pH 4 to pH 6
  10. dry with materialThe combined organic layers were dried (MgSO4)
  11. customthe solvent was removed in vacuo

出典と根拠

ORDレコード
ord-c2901c45e1bf47ccb5a2ade354312481
出典データセット
uspto-grants-2003_12
特許番号
US06670359B2

反応ノート

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