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

温度

-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 (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.

1. temperatureto warm to rt over 1 h
2. stirringstirred for 1 h at rt
3. extractionThe aq. layer was extracted with EtOAc (2×150 mL)
4. washlayer was washed with brine (200 mL)
5. dry with materialThe organic layer was dried over MgSO4
6. filtrationfiltered
7. customthe solvent removed under reduced pressure
8. customPurification of the residue by FC (1:1 hept-EA)

ORDレコード

ord-39cb831c15c84561a45ac6c7c947f6fb

出典データセット

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08536209B2