2-(1,3-Dioxolan-2-yl)-1,3-thiazole-5-carboxylic acid → 2-Formylthiazole-5-carboxylic acid

HRID 588518Notes

Reaction equation

HRID 588518 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[S:7][C:8]([C:11]([OH:13])=[O:12])=[CH:9][N:10]=1>Cl.CC(C)=O>[CH:2]([C:6]1[S:7][C:8]([C:11]([OH:13])=[O:12])=[CH:9][N:10]=1)=[O:1]

Participants

4

Reactant 1

HCID 184418922-(1,3-Dioxolan-2-yl)-1,3-thiazole-5-carboxylic acid

Product 1

HCID 184418962-Formylthiazole-5-carboxylic acidYield 229.1%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 313Hydrochloric AcidSolvent

Procedure

A solution of 2-(1,3-dioxolan-2-yl)thiazole-5-carboxylic acid (20 g, 0.1 mol) in hydrochloric acid (1000 mL, 3 N) and acetone (1000 mL) was heated to reflux for 6 h. The solution was then extracted with ether (5×500 mL). The combined organic phases were dried (Na2SO4) and concentrated. Flash column chromatography (petroleum ether: EtOAc, 100:1 to 5:1) afforded 2-formylthiazole-5-carboxylic acid (36 g, 76%). %). 1H NMR (DMSO-d6, 300 MHz) δ 13.90 (br, 1H), 9.92 (s, 1H), 8.63 (s, 1H).

Workup

  1. temperatureto reflux for 6 h
  2. extractionThe solution was then extracted with ether (5×500 mL)
  3. dry with materialThe combined organic phases were dried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e4b449348f9c4560bf43940740de5724
Source dataset
uspto-grants-2016_01
Patent number
US09227951B2

Reaction notes

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