Methanol → 3-[5-(3-Methoxy-3-oxopropyl)-1,3-oxazol-2-yl]benzoic acid

HRID 348883

Reaction equation

HRID 348883 reaction equation
[C:1]([CH2:4][CH2:5][C:6]1[O:10][C:9]([C:11]2[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=2)[C:14]([OH:16])=[O:15])=[N:8][CH:7]=1)([OH:3])=[O:2].S(Cl)(Cl)=O.[CH3:24]O>>[CH3:24][O:2][C:1](=[O:3])[CH2:4][CH2:5][C:6]1[O:10][C:9]([C:11]2[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=2)[C:14]([OH:16])=[O:15])=[N:8][CH:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 210856903-[5-(2-Carboxyethyl)-1,3-oxazol-2-yl]benzoic acid

Product 1

HCID 210856913-[5-(3-Methoxy-3-oxopropyl)-1,3-oxazol-2-yl]benzoic acid

Procedure

To 3-[5-(2-carboxyethyl)-1,3-oxazol-2-yl]benzoic acid (317 mg, 1.2 mmol) in methanol (5 mL) is added thionyl chloride (4.4 μL, 0.06 mmol), and the reaction is stirred at room temperature 16 h. The solution is concentrated under reduced pressure to give the title compound. ESI MS m/z 274.1 [M−H]−.

Workup

  1. concentrationThe solution is concentrated under reduced pressure

Sources & evidence

ORD record
ord-c873f96b4449495daa857fc40856a66d
Source dataset
uspto-grants-2007_02
Patent number
US07176242B2

Linked notes

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