Sodium borohydride → 2-(Thiazol-2-ylmethoxy)ethanol
Reaction equation
C[O:2][C:3](=O)[CH2:4][O:5][CH2:6][C:7]1[S:8][CH:9]=[CH:10][N:11]=1.[BH4-].[Na+]>CO>[S:8]1[CH:9]=[CH:10][N:11]=[C:7]1[CH2:6][O:5][CH2:4][CH2:3][OH:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A cooled (0° C.) sol. of (thiazol-2-ylmethoxy)acetic acid methyl ester (31.0 g, 165.6 mmol) in MeOH (830 mL) was treated portionwise with NaBH4 (31.0 g, 1.66 mol). The reaction mixture was allowed to warm to rt over 1 h. The mixture was then quenched with water, and extracted with CH2Cl2 (3×). The combined org. layers were dried over MgSO4, filtered, and the solvents were removed under reduced pressure to give the title compound as an orange oil (22.9 g, 87%) that was not further purified. LC-MS: tR=0.44 min, ES+: 160.19.
Workup
- customThe mixture was then quenched with water
- extractionextracted with CH2Cl2 (3×)
- dry with materiallayers were dried over MgSO4
- filtrationfiltered
- customthe solvents were removed under reduced pressure
Sources & evidence
- ORD record
- ord-e6118091d65542f7b97b4240cc204a09
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08138340B2
Reaction notes
Loading…