Ethyl Acetate → HCID 14041487, compound

HRID 2364675Notes

Reaction equation

HRID 2364675 reaction equation
[CH:1]12[O:7][CH:6]1[CH2:5][CH:4]=[CH:3][CH2:2]2.[Cl-].[NH4+].[N-:10]=[N+:11]=[N-:12].[Na+].C(OCC)(=O)C>CO.O.C(OCC)C>[N:10]([C@H:1]1[C@H:6]([OH:7])[CH2:5][CH:4]=[CH:3][CH2:2]1)=[N+:11]=[N-:12]

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 973417-Oxabicyclo[4.1.0]hept-3-ene

Product 1

HCID 14041487HCID 14041487, compoundYield 60%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

7-Oxabicyclo[4.1.0]hept-3-ene 3b (3.50 g, 36.40 mmol), ammonium chloride (4.90 g, 91 mmol) and sodium azide (5.90 g, 91 mmol) were dissolved in 200 mL of the mixture solvent of methanol and water (V/V=9:1), the reaction solution was heated to reflux for 2 hours. The resulting solution was added with 500 mL of ethyl acetate, 200 mL of ethyl ether and 50 mL of water successively, seperated. The organic phase was dried over anhydrous magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure to obtain the title compound (1R,6R)-6-azidocyclohex-3-en-1-ol 3c (3 g, yield: 60.0%) as a yellow oil.

Workup

  1. temperaturethe reaction solution was heated
  2. temperatureto reflux for 2 hours
  3. customseperated
  4. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-143d974a88ca458ab7593a7cb377df75
Source dataset
uspto-grants-2014_04
Patent number
US08691822B2

Reaction notes

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