Sodium borohydride → 1-(2-Chloropyrimidin-4-yl)ethanol
Reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:4][N:3]=1.[BH4-].[Na+]>CO.CCOC(C)=O>[Cl:1][C:2]1[N:7]=[C:6]([CH:8]([OH:10])[CH3:9])[CH:5]=[CH:4][N:3]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 1-(2-chloropyrimidin-4-yl)ethanone (600 mg, 3.83 mmol) in MeOH (5 mL) at 0° C. was added sodium borohydride (145 mg, 3.83 mmol) and stirred for 30 min. The solution was diluted with EtOAc, washed with brine, dried with MgSO4, filtered, and concentrated to dryness to afford 1-(2-chloropyrimidin-4-yl)ethanol (220 mg, 1.39 mmol, 36% yield). MS ESI: [M+H]+ m/z 159.0. 1H NMR (500 MHz, CDCl3) δ 8.60 (d, J=5.1, 1H), 7.39 (d, J=5.1, 1H), 4.87 (q, J=6.6, 1H), 1.53 (m, 3H).
Workup
- washwashed with brine
- dry with materialdried with MgSO4
- filtrationfiltered
- concentrationconcentrated to dryness
Sources & evidence
- ORD record
- ord-f05c26f4a96d4a1bad22127658f72275
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08759366B2
Reaction notes
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