Water → HCID 22064029, 화합물

HRID 131138노트

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HRID 131138 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

HCID 22064029HCID 22064029, 화합물수율 66%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-ebe9f48ca0a24c5bb3346a94a58c6f38
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384943B2

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