Nitrogen → [4-(Chloromethyl)-1,3-thiazol-2-yl]methanol

Participants

Reaction Conditions

Reaction Steps

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-carboxylic acid ethyl ester (8.51 g, 41.38 mmol) in THF (413 mL) was treated at −78° C. with DiBAL (124 mL of a 1M sol in THF, 124 mmol) and the reaction mixture was stirred for 1 h at −78° C. The mixture was then allowed to warm up to rt and poured into a Rochelle's salt solution. After stirring for 1 h, the layers were separated and the aq. layer extracted with EA. The combined org. extracts were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. Purification by FC (hept-EA) gave the title compound as a yellow oil. TLC:rf (1:1 hept-EA)=0.29. LC-MS-conditions 02: tR=0.59 min; [M+H]+=164.08.

Provenance & Evidence