Tetrahydrofuran → HCID 22998961, compound

HRID 2303928Notes

Reaction equation

HRID 2303928 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:12][CH2:11][C:10]3[N:13]=[CH:14][CH:15]=[CH:16][C:9]=3[C:8](=[O:17])[C:7]=2[CH:18]=1.[Cl-].[NH4+].C(OCC)(=O)C.[CH2:27]1[CH2:31]OC[CH2:28]1>>[CH:28]1([C:8]2([OH:17])[C:7]3[CH:18]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=3[O:12][CH2:11][C:10]3[N:13]=[CH:14][CH:15]=[CH:16][C:9]2=3)[CH2:27][CH2:31]1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 9813533HCID 9813533, compound

Product 1

HCID 22998961HCID 22998961, compound

Procedure

To a solution of 5,11-dihydro-7-methoxypyrido[2,3-c][1]benzoxepin-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-methoxypyrido[2,3-c][1]benzoxepin-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-77cd670e18a0429091596e1ac7f9d446
Source dataset
uspto-grants-2002_08
Patent number
US06433165B1

Reaction notes

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