Diethyl Ether → HCID 67469124, compound

To a mixture of 2-bromo-4-methylthiazole-5-carbaldehyde of preparation 98 (1.8 g, 8.8 mmol) in dry THF (50 mL) was added dropwise MeMgBr in Et2O (3M, 2.9 mL, 8.8 mmol) at −40° C. under N2. After the addition, the mixture was stirred at room temperature for 1 hr. TLC (petroleum ether/EtOAc=5:1) showed most of the starting material was consumed. To the reaction mixture was added saturated NH4Cl (60 mL). The mixture was extracted with EtOAc (50 mL×2). The combined organic layers were washed with brine (80 mL), dried over sodium sulfate and concentrated in vacuum. The residue was purified by a Biotage silica gel cartridge (EA/PE 48%, Rf=0.5) to give the title compound as a yellow oil (1.7 g, 87%).

1. additionAfter the addition
2. customwas consumed
3. additionTo the reaction mixture was added saturated NH4Cl (60 mL)
4. extractionThe mixture was extracted with EtOAc (50 mL×2)
5. washThe combined organic layers were washed with brine (80 mL)
6. dry with materialdried over sodium sulfate
7. concentrationconcentrated in vacuum
8. customThe residue was purified by a Biotage silica gel cartridge (EA/PE 48%, Rf=0.5)

ORD record

ord-204855a9873b4462a07b8ee0fc715e4b

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08916593B2