Tetrahydrofuran → HCID 18675743, compound

HRID 556897Notes

Reaction equation

HRID 556897 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-c170414f4f0b463da412a9177606508f
Source dataset
uspto-grants-2011_11
Patent number
US08058287B2

Reaction notes

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