Water → (2R)-2'-fluoro-2-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)propiophenone

HRID 2396999노트

반응식

HRID 2396999 반응식
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C@H:8]([CH3:17])[C:9](N1CCOCC1)=[O:10].[Mg].[Cl-].[NH4+].O.Br[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[F:29]>O1CCCC1.C(Br)C>[F:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[C:9](=[O:10])[C@H:8]([O:7][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][O:1]1)[CH3:17]

참가 물질

8

반응물 5

HCID 962WaterHCID 25517Ammonium ChlorideHCID 612591-Bromo-2-fluorobenzeneHCID 5462224MagnesiumHCID 10977653(2R)-1-morpholino-2-((tetrahydro-2H-pyran-2-yl)oxy)propan-1-one

생성물 1

HCID 10037839(2R)-2'-fluoro-2-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)propiophenone

시약·촉매·용매 2

HCID 6332Ethyl Bromide용매HCID 8028Tetrahydrofuran용매

실험 절차

In tetrahydrofuran (100 ml) were dissolved 1-bromo-2-fluorobenzene (5.6 ml), ethyl bromide (0.37 ml) and 4-[(2R)-2-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)propionyl]morpholine (11.3 g). To the mixture was added magnesium (turnings, 1.33 g). The mixture was stirred for 2 hours at room temperature. To the reaction mixture were added a saturated aqueous ammonium chloride solution (40 ml) and water (40 ml). The mixture was extracted with ethyl acetate (200 ml). The organic layer was washed with water, dried over magnesium sulfate and distilled under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=10:1→8:1) to give (2R)-2'-fluoro-2-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)propiophenone (8.7 g) as a pale yellow oily substance.

후처리

  1. extractionThe mixture was extracted with ethyl acetate (200 ml)
  2. washThe organic layer was washed with water
  3. dry with materialdried over magnesium sulfate
  4. distillationdistilled under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=10:1→8:1)

출처 및 근거

ORD 기록
ord-02e1b95b212849e39cdf7471c05b39fc
출처 데이터셋
uspto-grants-1996_02
특허 번호
US05495024

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