Hydrochloric Acid → HCID 69672418, compound

HRID 2406396Notes

Reaction equation

HRID 2406396 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:6]=1[C:12]1[O:16][N:15]=[CH:14][CH:13]=1)[CH:2]=[CH2:3].[O-]CC.[Na+].Cl>C(O)C>[CH2:1]([O:4][C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:6]=1[C:12](=[O:16])[CH2:13][C:14]#[N:15])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2723922Sodium ethoxideHCID 696723875-[2-(Allyloxy)-4-methylphenyl]isoxazole

Product 1

HCID 69672418HCID 69672418, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred suspension of 5-[2-(allyloxy)-4-methylphenyl]isoxazole (Step 3, 7.3 g, 33.8 mmol) in ethanol (40 mL) was added sodium ethoxide (21% solution in ethanol, 40 mL, 110 mmol) and the reaction was stirred at room temperature for 3 hours. The reaction was acidified to pH 2 with hydrochloric acid (2N, aqueous) and the solid was filtered off and air dried for 1 hour to give the title compound as an off-white solid, 4.8 g, in a 66% yield. LCMS (2 min acidic) 1.12 min 51-100% pure by UV, ES+/AP+ 216, ES−/AP− 214.

Workup

  1. filtrationthe solid was filtered off
  2. customair dried for 1 hour

Sources & evidence

ORD record
ord-801bb784ddcf458aa2cde49999351450
Source dataset
uspto-grants-2014_08
Patent number
US08809363B2

Reaction notes

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