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

HRID 1491711Notes

Reaction equation

HRID 1491711 reaction equation
[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]

Participants

8

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6332Ethyl BromideSolventHCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-83b81ba38064483789ede7ca10f146f1
Source dataset
uspto-grants-1994_12
Patent number
US05371100

Reaction notes

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