Aluminium lithium hydride → 1-(2-Chloropyridin-3-yl)propane-1,3-diol
Reaction equation
C([O:3][C:4](=O)[CH2:5][CH:6]([C:8]1[C:9]([Cl:14])=[N:10][CH:11]=[CH:12][CH:13]=1)[OH:7])C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Cl:14][C:9]1[C:8]([CH:6]([OH:7])[CH2:5][CH2:4][OH:3])=[CH:13][CH:12]=[CH:11][N:10]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 3-(2-chloropyridin-3-yl)-3-hydroxypropanoic acid ethyl ester (66.7 mmol) in 47 mL THF was added a suspension of LiAlH4 (100 mmol) in 219 mL THF at 0° C. The mixture was stirred at 0° C. for 1 h and was then quenched by adding consecutively 3.8 mL water, 3.8 mL 15% aq. NaOH solution and 11.4 mL water. The mixture was filtrated and the residue was washed with MTBE and EtOAc. The filtrate was dried over MgSO4 and concentrated in vacuo to obtain the desired product as yellow solid.
Workup
- customwas then quenched
- additionby adding consecutively 3.8 mL water, 3.8 mL 15% aq. NaOH solution and 11.4 mL water
- filtrationThe mixture was filtrated
- washthe residue was washed with MTBE and EtOAc
- dry with materialThe filtrate was dried over MgSO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-93078206fa4747998b8ccc0eb17bcd97
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09409917B2
Reaction notes
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