Hydrochloric Acid → 1-(4-Chloromethyl-thiazol-2-yl)-ethanol

Temperature

0 °C

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 4-chloromethyl-thiazole-2-carbaldehyde (1.05 g, 6.49 mmol) in CH2Cl2 (65.0 mL) was treated at 0° C. with trimethylaluminum (32.45 mL of a 1M solution in heptane, 32.45 mmol). The reaction mixture was then stirred at 0° C. for 45 min. CH2Cl2 (100.0 mL) followed by sat. aq. NH4Cl (80 mL) was then added. The mixture was then treated with 1N HCl (100 mL) and the aq. layer was extracted with CH2Cl2 (100 mL). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure to give the title compound as a yellow oil. LC-MS-conditions 02: tR=0.66 min, [M+H]+=178.50.

1. additionwas then added
2. extractionthe aq. layer was extracted with CH2Cl2 (100 mL)
3. dry with materialextracts were dried over MgSO4
4. filtrationfiltered
5. customthe solvents were removed under reduced pressure

ORD record

ord-a2a64d281aee43f6bbf4941f7c0a7e65

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08288419B2