Aluminium lithium hydride → Thieno[3,2-c]pyridin-2-ylmethanol
Reaction equation
[S:1]1[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[CH:3]=[C:2]1[C:10](OC)=[O:11].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[S:1]1[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[CH:3]=[C:2]1[CH2:10][OH:11]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of methyl thieno[3,2-c]pyridine-2-carboxylate (D-2) (15 g, 77.6 mmol) in anhydrous THF (250 mL) was added LiAlH4 (4.42 g, 116.4 mmol) in portions at 0° C. The suspension was stirred at 0° C. for 1 h and then quenched by adding saturated aqueous NH4Cl and filtered. The filtrate was washed with brine and concentrated. The residue was used in the next step without any further purification (10.3 g).
Workup
- customquenched
- additionby adding saturated aqueous NH4Cl
- filtrationfiltered
- washThe filtrate was washed with brine
- concentrationconcentrated
- customThe residue was used in the next step without any further purification (10.3 g)
Sources & evidence
- ORD record
- ord-6b7c4c9efd8e46a58e4caeac72e0c018
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08987269B2
Reaction notes
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