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

Temperatur

-78 °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-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.

1. temperatureto warm up to rt
2. stirringAfter stirring for 1 h
3. customthe layers were separated
4. extractionthe aq. layer extracted with EA
5. washextracts were washed with brine
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customPurification by FC (hept-EA)

ORD-Eintrag

ord-0d5d134bfc3c47feac04c0f6d6b82935

Quelldatensatz

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08563714B2