Acetic acid, 2-oxo-, methyl ester → Methyl 5-oxazolecarboxylate

HRID 1637573Notes

Reaction equation

HRID 1637573 reaction equation
[C:1]([CH:5]([CH:7](C(OC)=O)O)[OH:6])([O:3][CH3:4])=[O:2].C(OC)(=O)C=O.S([CH2:29][N+:30]#[C-])(C1C=CC(C)=CC=1)(=O)=O>>[O:6]1[C:5]([C:1]([O:3][CH3:4])=[O:2])=[CH:7][N:30]=[CH:29]1

Participants

4

Reactant 3

HCID 70205Acetic acid, 2-oxo-, methyl esterHCID 79067Dimethyl 2,3-dihydroxybutanedioateHCID 161915Tosylmethyl isocyanide

Product 1

HCID 2724619Methyl 5-oxazolecarboxylate

Procedure

For B.4274, dimethyl tartrate was oxidised11 to methyl glyoxylate which reacted 12 with tosylmethyl isocyanide to give methyl oxazole-5-carboxylate.13This was reduced by lithium aluminium hydride by the method of Fallab14 to the alcohol.15

Sources & evidence

ORD record
ord-c5a02cef02ce444bae5c507885a2528b
Source dataset
uspto-grants-2000_03
Patent number
US06043228

Reaction notes

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