Hydrazine hydrate (1:1) → HCID 178450770, compound

HRID 538725Notes

Reaction equation

HRID 538725 reaction equation
O=[C:2]([C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:13][CH:12]=1)[CH2:3][C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].CC(OC([N:33]([CH3:35])C)N(C)C)(C)C.O.[NH2:37]N>O1CCCC1>[O:17]([C:14]1[CH:15]=[CH:16][C:11]([C:2]2[C:3]([C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])=[CH:35][NH:33][N:37]=2)=[CH:12][CH:13]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 79885tert-Butoxy bis(dimethylamino)methaneHCID 86617051HCID 86617051, compound

Product 1

HCID 178450770HCID 178450770, compoundYield 48.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To tert-Butyl 3-oxo-3-(4-phenoxyphenyl)propanoate (559 mg, 1.80 mmol) in tetrahydrofuran, was added Bredereck's reagent (1.18 mL, 5.70 mmol). The reaction mixture was stirred for 6 hours under nitrogen at reflux. The reaction mixture was concentrated in vacuo and taken up in EtOH (5 mL). Hydrazine monohydrate (79 μL, 1.63 mmol) was added and the reaction mixture was heated at reflux for 16 hours. The crude mixture was concentrated in vacuo, taken up in EtOAc, washed with water, a saturated aqueous solution of NaHCO3 and brine. The organic phase was dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (eluting with 40% EtOAc in petroleum ether) to afford the title compound (264 mg, 48% yield). MS (ES+) m/e=337. 1H NMR (CDCl3) δH 1.52 (9H, s), 7.04 (2H, d), 7.06 (2H, d), 7.16 (1H, t), 7.38 (2H, t), 7.66 (2H, d), 7.95 (1H, s), 10.90 (1H, br s).

Workup

  1. temperatureat reflux
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. temperaturethe reaction mixture was heated
  4. temperatureat reflux for 16 hours
  5. concentrationThe crude mixture was concentrated in vacuo
  6. washwashed with water
  7. dry with materialThe organic phase was dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by silica gel chromatography (eluting with 40% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-0b1a084b162041d9980d26fc289b66c3
Source dataset
uspto-grants-2014_10
Patent number
US08865751B2

Reaction notes

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