Tetrahydrofuran → HCID 18675743, compound

HRID 1983612Notes

Reaction equation

HRID 1983612 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-4d83629007534a24880255f7d28e157b
Source dataset
uspto-grants-2009_06
Patent number
US07541365B2

Reaction notes

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