Potassium sodium tartarate → HCID 18673047, compound

Diisobutylaluminum hydride (1.5M in toluene; 6.5 mL, 9.8 mmol) was added dropwise to a solution of 2-(1-methylethyl)-4-methylthiazole-5-carboxylic acid ethyl ester (Example 9; 1.0 g, 4.7 mmol) in toluene (8 mL) at −75° C. After 15 min, the cold reaction mixture was treated with saturated aqueous potassium sodium tartrate (15 mL) and the reaction mixture was allowed to warm to room temperature. The reaction mixture was filtered and the solids were washed thoroughly with toluene. The combined filtrates were washed with brine (50 mL) and the brine layer was back-washed with toluene (3×35 mL) and ethyl acetate (2×35 mL) to extract the product completely. The combined organic layers were dried (MgSO4), filtered and evaporated under reduced pressure to give 2-(1-methylethyl)-4-methylthiazole-5-methanol (742 mg, 92% yield).

1. customthe cold reaction mixture
2. filtrationThe reaction mixture was filtered
3. washthe solids were washed thoroughly with toluene
4. washThe combined filtrates were washed with brine (50 mL)
5. washthe brine layer was back-washed with toluene (3×35 mL) and ethyl acetate (2×35 mL)
6. extractionto extract the product completely
7. dry with materialThe combined organic layers were dried (MgSO4)
8. filtrationfiltered
9. customevaporated under reduced pressure

ORD record

ord-ea082e631e1c49f7bbce0e67a20303ff

Source dataset

uspto-grants-2003_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06515124B2