Methanol → HCID 54319561, compound

HRID 2379012Notes

Reaction equation

HRID 2379012 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:12][CH2:13][C@H:14]([CH:16]([CH3:18])[CH3:17])[N:15]=2)=[CH:7][CH:6]=1)=[O:4].[OH-].[K+].O.CO>C(OCC)C>[C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:12][CH2:13][C@H:14]([CH:16]([CH3:18])[CH3:17])[N:15]=2)=[CH:7][CH:6]=1)([OH:4])=[O:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14797Potassium HydroxideHCID 53860753HCID 53860753, compound

Product 1

HCID 54319561HCID 54319561, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 3 g of (S)-2-(4-[methoxycarbonyl]phenyl)-4-isopropyl-2-oxazoline, 3 g of potassium hydroxide, 5 ml of water and 50 ml of methanol is heated at 75° C. on an oil bath for 4 hours. The cooled mixture is treated with 10 ml of ice-cold 3N hydrochloric acid and the liberated acid is taken up in 150 ml of diethyl ether. The separated aqueous phase is back-extracted twice with 100 ml of diethyl ether each time. The combined organic phases are washed with 50 ml of 2N sodium carbonate solution and several times with water, dried over magnesium sulphate and concentrated. Recrystallization of the resulting crude product from ethanol yields (S)-2-(4-carboxyphenyl)-4-isopropyl-2-oxazoline.

Workup

  1. extractionThe separated aqueous phase is back-extracted twice with 100 ml of diethyl ether each time
  2. washThe combined organic phases are washed with 50 ml of 2N sodium carbonate solution and several times with water
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated
  5. customRecrystallization of the resulting crude product from ethanol

Sources & evidence

ORD record
ord-4a4a5d6716d04b378844e7d6fc54ea5a
Source dataset
uspto-grants-1994_11
Patent number
US05360577

Reaction notes

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