Ethyl 6-Bromopicolinate → (6-Bromopyridin-2-yl)methanol
Reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8](OCC)=[O:9])[CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Br:1][C:2]1[N:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
The ester from Step 2 was dissolved in THF (1.2 L), the solution cooled to 0° C., and under a N2 atmosphere, there was slowly added LiAlH4 (20 g) over 1 h. After a further 30 min., the mixture was quenched carefully with sat'd aqueous NH4Cl (250 mL). The granular salts were filtered off, washed with EtOAc, and the filtrate was dried over MgSO4, and evaporated to afford the title alcohol (85 g) as an oil.
Workup
- customover 1 h
- customthe mixture was quenched carefully with sat'd aqueous NH4Cl (250 mL)
- filtrationThe granular salts were filtered off
- washwashed with EtOAc
- dry with materialthe filtrate was dried over MgSO4
- customevaporated
Sources & evidence
- ORD record
- ord-bc5ec88c08ab4ae7a29999735deccf57
- Source dataset
- uspto-grants-1996_09
- Patent number
- US05552437
Reaction notes
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