Diethyl Ether → Ethyl 2-(2-hydroxypropan-2-yl)oxazole-4-carboxylate

HRID 1409305Notes

Reaction equation

HRID 1409305 reaction equation
[C:1]([C:4]1[O:5][CH:6]=[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[N:8]=1)(=[O:3])[CH3:2].[CH3:14][Mg]I.CCOCC>C1COCC1>[OH:3][C:1]([C:4]1[O:5][CH:6]=[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[N:8]=1)([CH3:14])[CH3:2]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 66820192Ethyl 2-acetyloxazole-4-carboxylateHCID 178418373HCID 178418373, compound

Product 1

HCID 83384756Ethyl 2-(2-hydroxypropan-2-yl)oxazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a flask containing a solution of ethyl 2-acetyloxazole-4-carboxylate (2.0 g, 10.9 mmol) in THF (50 ml), 3M solution of MeMgI in ether (5.0 ml, 13.11 mmol) was added at 0° C. The resulting mixture was stirred at RT for 5 h. The mixture was quenched with aqueous NH4Cl solution and extracted with EtOAc. The organic layer was concentrated and purified with flash chromatography. Yield 1.0 g. 1H-NMR (400 MHz; CDCl3): δ 1.59 (s, 3H), 1.66 (s, 6H), 2.70 (s, 1H), 4.39 (q, 2H), 8.17 (s, 1H).

Workup

  1. additionwas added at 0° C
  2. customThe mixture was quenched with aqueous NH4Cl solution
  3. extractionextracted with EtOAc
  4. concentrationThe organic layer was concentrated
  5. custompurified with flash chromatography

Sources & evidence

ORD record
ord-a9c94cf678cc4276b27fcf603245f0ef
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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