Reaktion #170015

Reaktionsgleichung

NH4Cl

N2

methyl 2-(chloromethyl)oxazole-4-carboxylate

methylmagnesium chloride

THF

THF

→

title compound

2-(2-(Chloromethyl)oxazol-4-yl)propan-2-ol

Reaktionsbedingungen

Aufarbeitung

1. 1
   ExtraktionIt was extracted with EA (3×200 mL)
2. 2
   Waschenlayers were washed with brine (300 mL)
3. 3
   Trocknendried over MgSO4
4. 4
   Filtrationfiltered
5. 5
   Sonstigethe solvent was removed under reduced pressure
6. 6
   SonstigePurification of the residue by FC (6:4 hept-EA)

Vorschrift

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of methyl 2-(chloromethyl)oxazole-4-carboxylate (Organic Process Research & Development 2001, 5, 37-44) (13.00 g, 74.04 mmol) in THF (433 mL) was treated dropwise at 0° C. with methylmagnesium chloride (51.8 mL of a 3.0 M solution in THF, 155.49 mmol) and the resulting orange solution was stirred for 1.5 h at 0° C. The reaction mixture was carefully poured over an ice-chilled sat. aq. NH4Cl solution (300 mL). It was extracted with EA (3×200 mL) and the combined org. layers were washed with brine (300 mL), dried over MgSO4, filtered and the solvent was removed under reduced pressure. Purification of the residue by FC (6:4 hept-EA) gave the title compound as a yellow oil: TLC: rf (6:4 hept-EA)=0.24. LC-MS-conditions 06: tR=0.49 min.

Quelle