Potassium sodium tartarate → HCID 10909824, compound

Diisobutylaluminum hydride (1.5M in toluene; 2.4 mL, 3.6 mmol) was added dropwise over 10 min to a solution of 4-(1-methylethyl)thiazole-5-carboxylic acid ethyl ester (Example 8; 650 mg, 3.26 mmol) in toluene (5 mL) at −75° C. After 80 min, a second portion of diisobutylaluminum hydride (1.5M in toluene; 1.1 mL, 1.65 mmol) was added dropwise over 5 min at −75° C. After 20 min the cold reaction mixture was treated with saturated aqueous potassium sodium tartrate (5 mL) and the reaction mixture was allowed to warm to room temperature over 15 min. The liquid phase was decanted from the colorless solids and the filter cake was washed with toluene. The combined organic layers were washed with 5% aqueous potassium sodium tartrate (20 mL) and brine, then dried (MgSO4), filtered and evaporated in vacuo. The resulting residue was chromatographed over silica gel (0-25% ethyl acetate/hexanes) to give 4-(1-methylethyl)thiazole-5-methanol (350 mg, 69% yield).

1. customAfter 20 min the cold reaction mixture
2. customThe liquid phase was decanted from the colorless solids
3. washthe filter cake was washed with toluene
4. washThe combined organic layers were washed with 5% aqueous potassium sodium tartrate (20 mL) and brine
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. customevaporated in vacuo
8. customThe resulting residue was chromatographed over silica gel (0-25% ethyl acetate/hexanes)

ORD record

ord-28a3aecd69d24610b5741a0cbd3a3eda

Source dataset

uspto-grants-2003_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06515124B2