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

HRID 1491711

反応式

HRID 1491711 の反応式
[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]

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6332Ethyl Bromide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-83b81ba38064483789ede7ca10f146f1
出典データセット
uspto-grants-1994_12
特許番号
US05371100

関連ノート

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