Tetrahydrofuran → HCID 18675743, compound

HRID 1635527Notes

Reaction equation

HRID 1635527 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[CH2:9][C:10](=[O:18])[C:11]3[C:12]([O:17][C:7]=2[CH:6]=[CH:5][CH:4]=1)=[N:13][CH:14]=[CH:15][CH:16]=3.[Cl-].[NH4+].C(OCC)(=O)C.[CH2:27]1[CH2:31]OC[CH2:28]1>>[CH:28]1([C:10]2([OH:18])[C:11]3[C:12](=[N:13][CH:14]=[CH:15][CH:16]=3)[O:17][C:7]3[CH:6]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:8]=3[CH2:9]2)[CH2:27][CH2:31]1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 18675697HCID 18675697, compound

Product 1

HCID 18675743HCID 18675743, compound

Procedure

To a solution of 5,11-dihydro-7-methoxy [1]benzoxepino[2,3-b]pyridin-5-one (5.0 g) in THF (50 ml) was added 1.1M cyclopropylmagnesium bromide THF solution (25 ml) at 0° C. The reaction mixture was warmed to room temperature, and stirred for 30 minutes. Aqueous ammonium chloride and ethyl acetate were added to the reaction mixture, the organic layer was separated and washed with saturated aqueous sodium chloride, and dried with magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was filtered and washed with ethyl acetate-hexane (1:2) to give 5-cyclopropyl-5,11-dihydro-7-methoxy[1]benzoxepino[2,3-b]pyridin-5-ol (5.0 g).

Workup

  1. customthe organic layer was separated
  2. washwashed with saturated aqueous sodium chloride
  3. dry with materialdried with magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. filtrationThe residue was filtered
  6. washwashed with ethyl acetate-hexane (1:2)

Sources & evidence

ORD record
ord-928dad9be19f443f9c5edab62bebff47
Source dataset
uspto-grants-2003_01
Patent number
US06509346B2

Reaction notes

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