반응 #71071

반응 방정식

Rochelle's salt

N2

4-chloromethyl-thiazole-2-carboxylic acid ethyl ester

DiBAL

→

title compound

(4-Chloromethyl-thiazol-2-yl)-methanol

용매

THF

THF

반응 조건

후처리

1. 1
   온도to warm to rt over 1 h
2. 2
   workup.STIRRINGstirred for 1 h at rt
3. 3
   추출The aq. layer was extracted with EtOAc (2×150 mL)
4. 4
   세척layer was washed with brine (200 mL)
5. 5
   건조The organic layer was dried over MgSO4
6. 6
   여과filtered
7. 7
   기타the solvent removed under reduced pressure
8. 8
   기타Purification of the residue by FC (1:1 hept-EA)

실험 절차

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 (2.47 g, 12.03 mmol) in THF (120.0 mL) was treated at −78° C. with DiBAL (36.09 mL of a 1M sol in THF, 36.09 mmol) and the reaction mixture was stirred for 1 h at −78° C. and the allowed to warm to rt over 1 h. The reaction mixture was poured over a sat. aq. Rochelle's salt sol. and stirred for 1 h at rt. The aq. layer was extracted with EtOAc (2×150 mL) and the combined org. layer was washed with brine (200 mL). The organic layer was dried over MgSO4, filtered, and the solvent removed under reduced pressure. Purification of the residue by FC (1:1 hept-EA) gave the title compound as a light yellow oil. TLC:rf (1:1 hept-EA)=0.30. LC-MS-conditions 02: tR=0.59 min, [M+H]+=164.07.

출처