Diethyl Ether → HCID 18953733, compound
Reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[CH2:8]([Li])CCC.[CH3:13][O:14][CH2:15][CH2:16][O:17][CH2:18][O:19][CH2:20][CH2:21][CH2:22][C:23]1([O:29][CH2:30][O:31][CH2:32][CH2:33][O:34][CH3:35])CC[O:26][C:24]1=O.C[CH2:37][O:38]CC>CCCCCC>[CH3:35][O:34][CH2:33][CH2:32][O:31][CH2:30][O:29][CH:23]([CH:22]([C:37](=[O:38])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1)[CH2:21][CH:20]([O:19][CH2:18][O:17][CH2:16][CH2:15][O:14][CH3:13])[CH3:8])[CH:24]=[O:26]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -20 °C
Procedure
A solution of 18.96 g (0.12 mole) of 3-bromopyridine in 50 ml of ether is added dropwise into a 54.72 ml (0.11 mole) of 2.01M n-butyllithium in hexane in 550 ml of ether at -78° C. with stirring under argon over a period of 20 min. The mixture is stirred for another 1/2 h and a solution of 30.35 g (0.0902 mole) of 2-[3-(2-methoxyethoxymethoxy)propyl]-2-(2-methoxyethoxymethoxy)-γ-butyrolactone in 30 ml of ether is added dropwise over a period of 10 min. The mixture is stirred at -78° C. for 2 h, allowed to warm up to -20° C., quenched with 15 ml of saturated aqueous ammonium chloride and washed with water and brine. The ether layer is dried (MgSO4) and evaporated to give 2,5-bis-(2-methoxyethoxymethoxy)-3-nicotinoyl-hexan-1-one as an oil.
Workup
- stirringThe mixture is stirred for another 1/2 h
- stirringThe mixture is stirred at -78° C. for 2 h
- customquenched with 15 ml of saturated aqueous ammonium chloride
- washwashed with water and brine
- dry with materialThe ether layer is dried (MgSO4)
- customevaporated
Sources & evidence
- ORD record
- ord-a756c11a81654a0db320023eed030fcd
- Source dataset
- uspto-grants-1994_12
- Patent number
- US05371096
Reaction notes
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