Sodium borohydride → 3-(1,3-Thiazol-4-yl)propan-1-ol

Temperature

0 °C

NaBH4 (1.68 g, 44.4 mmol) was added to a sol. of 3-thiazol-4-yl-propionaldehyde (4.35 g, 29.3 mmol) in MeOH (80 mL) at 0° C. The mixture was stirred for 30 min at 0° C., then for 1 h at rt. The mixture was cooled to 0° C., and ice was added. The mixture was partially evaporated under reduced pressure, and the residue was diluted with EtOAc. This mixture was washed with water and brine. The org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (EtOAc/heptane 1:1→EtOAc→CH2Cl2/EtOAc 1:9) yielded the title compound (4.01 g, 93%). LC-MS: tR=0.34, ES+: 144.16.

1. waitfor 1 h at rt
2. temperatureThe mixture was cooled to 0° C.
3. additionice was added
4. customThe mixture was partially evaporated under reduced pressure
5. additionthe residue was diluted with EtOAc
6. washThis mixture was washed with water and brine
7. dry with materialextracts were dried over MgSO4
8. filtrationfiltered
9. customthe solvents were removed under reduced pressure
10. customPurification of the residue by FC (EtOAc/heptane 1:1→EtOAc→CH2Cl2/EtOAc 1:9)

ORD record

ord-ac05362e60d4419faaf349337e89f67e

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08138340B2