Hydrochloric Acid → HCID 44632534, compound

HRID 2362027Notes

Reaction equation

HRID 2362027 reaction equation
[C:1](Cl)(=O)C.[Na+].[Cl-].[Cl:7][C:8]1[CH:9]=[C:10]([C:15]2[CH2:19][CH:18]([CH2:20][C:21]([OH:23])=[O:22])[O:17][N:16]=2)[CH:11]=[CH:12][C:13]=1[Cl:14].Cl>CO>[CH3:1][O:22][C:21](=[O:23])[CH2:20][CH:18]1[O:17][N:16]=[C:15]([C:10]2[CH:11]=[CH:12][C:13]([Cl:14])=[C:8]([Cl:7])[CH:9]=2)[CH2:19]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 6367Acetyl chlorideHCID 44634451HCID 44634451, compound

Product 1

HCID 44632534HCID 44632534, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Acetyl chloride (5 eq) was added to MeOH (50 vol) externally cooled with a mixture saturated aqueous NaCl solution and ice. After 10 minutes the solution was warmed to room temperature. After a further 90 minutes, [3-(3,4-dichloro-phenyl)-4,5-dihydro-isoxazol-5-yl]-acetic acid (1.0 eq) in MeOH (25 vol) was added to the hydrogen chloride methanolic solution and stirred for 16 hours. The solvent was concentrated under reduced pressure and the residue was purified by flash column chromatography (eluent: [3:7] EtOAc:heptane) to afford [3-(3,4-dichloro-phenyl)-4,5-dihydro-isoxazol-5-yl]-acetic acid methyl ester.

Workup

  1. concentrationThe solvent was concentrated under reduced pressure
  2. customthe residue was purified by flash column chromatography (eluent: [3:7] EtOAc:heptane)

Sources & evidence

ORD record
ord-6be1496613f74244aff72747137e9b63
Source dataset
uspto-grants-2014_04
Patent number
US08691824B2

Reaction notes

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