Reaktion #71102

Reaktionsgleichung

Ms-Cl

N2

[2-(2-methyl-[1,3]dioxolan-2-yl)-thiazol-5-yl]-methanol

Et3N

→

title compound

5-Chloromethyl-2-(2-methyl-[1,3]dioxolan-2-yl)-thiazole

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe reaction mixture was quenched with water (10 mL)
2. 2
   Extraktionextracted with CH2Cl2 (10 mL)
3. 3
   Trocknenextracts were dried over Na2SO4
4. 4
   Filtrationfiltered
5. 5
   Sonstigethe solvents were removed under reduced pressure
6. 6
   SonstigePurification of the residue by FC (5:1 to 2:1 hept-EA)

Vorschrift

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of [2-(2-methyl-[1,3]dioxolan-2-yl)-thiazol-5-yl]-methanol (560 mg, 2.78 mmol) in dry CH2Cl2 (5.0 mL) was treated at 0° C. with Et3N (0.50 mL, 3.60 mmol) followed by DMAP (34 mg, 0.28 mmol) and Ms-Cl (0.28 mL, 3.51 mmol). After stirring at 0° C. for 1 h, the reaction mixture was quenched with water (10 mL), extracted with CH2Cl2 (10 mL) and the combined org. extracts were dried over Na2SO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (5:1 to 2:1 hept-EA) gave the title compound as a pale yellow oil. TLC:rf (1:2 hept-EA)=0.50. LC-MS-conditions 01: tR=0.81 min; [M+H]+=219.89.

Quelle