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

HRID 14092Notes

Reaction equation

HRID 14092 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-aefa3b74c30b479da2d952052a0e8df6
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Reaction notes

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