Ethyl Acetate → HCID 22998966, compound

HRID 242523Notes

Reaction equation

HRID 242523 reaction equation
[CH3:1]CCCCC.C([Li])CCC.COC1[C:19]2[CH2:20][C:21](=O)[C:22]3[C:23]([O:28][C:18]=2[CH:17]=CC=1)=[N:24][CH:25]=[CH:26][CH:27]=3.[Cl-].[NH4+].[C:32]([O:35][CH2:36][CH3:37])(=O)[CH3:33]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[CH3:23][O:28][C:18]1[CH:17]=[CH:33][C:32]2[O:35][CH2:36][C:37]3[N:24]=[CH:25][CH:26]=[CH:27][C:22]=3[C:21](=[CH2:1])[C:20]=2[CH:19]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 18675697HCID 18675697, compoundHCID 178418244HCID 178418244, compound

Product 1

HCID 22998966HCID 22998966, compound

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of methyltriphenylphosphonium bromide (2.2 g) in THF (20 ml) was added 1.6M n-butyl lithium hexane solution (2.9 ml) at 0° C. for 30 minutes. To the reaction mixture cooled to 0° C. was added 5,11-dihydro-7-methoxy[1]benzoxepino[2,3-b]pyridin-5-one (1.0 g) dropwise as THF solution (5 ml), and the mixture was warmed to room temperature, and stirred for 3 hours. 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 purified by silica gel chromatography eluting with ethyl acetate-hexane (1:4) to give 5,11-dihydro-7-methoxy-5-methylenepyrido[2,3-c][1]benzoxepine (0.14 g).

Workup

  1. temperaturethe mixture was warmed to room temperature
  2. customthe organic layer was separated
  3. washwashed with saturated aqueous sodium chloride
  4. dry with materialdried with magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with ethyl acetate-hexane (1:4)

Sources & evidence

ORD record
ord-eb0ce55c7ea74b2297a6afb1e8cf5460
Source dataset
uspto-grants-2014_02
Patent number
US08653096B2

Reaction notes

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