Hydrochloric Acid → Methyl 2-(4-chlorophenyl)-4-(hydroxymethyl)-1,3-oxazole-5-carboxylate

HRID 508170Notes

Reaction equation

HRID 508170 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([C:18]([O:20][CH3:21])=[O:19])=[C:11]([CH2:13][O:14]COC)[N:12]=2)=[CH:4][CH:3]=1.Cl>CO.Cl.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:9][C:10]([C:18]([O:20][CH3:21])=[O:19])=[C:11]([CH2:13][OH:14])[N:12]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 58284400Methyl 2-(4-chlorophenyl)-4-[(methoxymethoxy)methyl]-1,3-oxazole-5-carboxylate

Product 1

HCID 58284345Methyl 2-(4-chlorophenyl)-4-(hydroxymethyl)-1,3-oxazole-5-carboxylate

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

144 mg (0.52 mmol) of the compound from Example 43A are initially charged in 0.5 ml of methanol, and 0.13 ml of 4 N hydrochloric acid are added. 3 drops of conc. hydrochloric acid are then added. The reaction mixture is stirred at RT for 8 h. The mixture is then diluted with about 5 ml of water and extracted three times with in each case 10 ml of diethyl ether. The combined organic phases are dried over magnesium sulfate and the solvent is removed on a rotary evaporator. The product obtained is used without further purification in the subsequent reaction.

Workup

  1. extractionextracted three times with in each case 10 ml of diethyl ether
  2. dry with materialThe combined organic phases are dried over magnesium sulfate
  3. customthe solvent is removed on a rotary evaporator
  4. customThe product obtained
  5. customis used without further purification in the subsequent reaction

Sources & evidence

ORD record
ord-2dadf170b3d6468882b6c489780934f2
Source dataset
uspto-grants-2015_08
Patent number
US09095582B2

Reaction notes

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