Hydrochloric Acid → 1-[5-(4-Nitro-pyrazol-1-ylmethyl)-isoxazol-3-yl]-ethanol

HRID 2064958Notes

Reaction equation

HRID 2064958 reaction equation
N#N.[N+:3]([C:6]1[CH:7]=[N:8][N:9]([CH2:11][C:12]2[O:16][N:15]=[C:14]([CH:17]=[O:18])[CH:13]=2)[CH:10]=1)([O-:5])=[O:4].[CH3:19][Al](C)C.[NH4+].[Cl-].Cl>C(Cl)Cl.CCCCCCC>[N+:3]([C:6]1[CH:7]=[N:8][N:9]([CH2:11][C:12]2[O:16][N:15]=[C:14]([CH:17]([OH:18])[CH3:19])[CH:13]=2)[CH:10]=1)([O-:5])=[O:4]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 947NitrogenHCID 25517Ammonium ChlorideHCID 16682925TrimethylaluminumHCID 86650887HCID 86650887, compound

Product 1

HCID 669288751-[5-(4-Nitro-pyrazol-1-ylmethyl)-isoxazol-3-yl]-ethanol

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8900HeptaneSolvent

Conditions

Temperature
0 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 5-(4-nitro-pyrazol-1-ylmethyl)-isoxazole-3-carbaldehyde (666 mg, 3.00 mmol) in CH2Cl2 (22.0 mL) was treated at 0° C. with trimethylaluminum (15 mL of a 1M solution in heptane, 15.00 mmol). The reaction mixture was then stirred at 0° C. for 2 h. CH2Cl2 (100.0 mL) followed by sat. aq. NH4Cl (50 mL) was then added. The mixture was then treated with 1N HCl and the aq. layer was extracted with CH2Cl2 (20 mL). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure to give the title compound as a green oil. LC-MS-conditions 02: tR=0.72 min.

Workup

  1. additionwas then added
  2. extractionthe aq. layer was extracted with CH2Cl2 (20 mL)
  3. dry with materialextracts were dried over MgSO4
  4. filtrationfiltered
  5. customthe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-de56d9487d734e7199e653dbf3038f46
Source dataset
uspto-grants-2012_10
Patent number
US08288419B2

Reaction notes

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