Diisopropylamine → HCID 68829402, compound
Reaction equation
[CH:1](NC(C)C)([CH3:3])[CH3:2].[Li]CCCC.[CH3:13][CH2:14][O:15][C:16]([CH3:18])=[O:17].C([C:26]1[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[CH:28][C:27]=1[CH:34]=[CH:35][N+:36]([O-:38])=[O:37])C1C=CC=CC=1.[CH2:39]1[CH2:43][O:42][CH2:41][CH2:40]1>>[CH2:14]([O:15][C:16](=[O:17])[CH2:18][CH:34]([C:27]1[CH:28]=[CH:29][C:30]([O:32][CH3:33])=[CH:31][C:26]=1[O:42][CH2:41][C:40]1[CH:39]=[CH:43][CH:3]=[CH:1][CH:2]=1)[CH2:35][N+:36]([O-:38])=[O:37])[CH3:13]Participants
Conditions
- Temperature
- -78 °C
Procedure
To a dry round bottom flask was added 3.5 mL of diisopropylamine and 20 mL THF under N2. The solution was cooled to −78° C. and stirred. A solution of n-BuLi (15 mL, 1.6 mL) was added and the reaction mixture was stirred for an additional 20 min. EtOAc (2.0 mL in 10 mL THF) was added slowly at −78° C. and the resulting solution was stirred for 20 min. 2-Benzyl-4-methoxy-1-(2-nitrovinyl)benzene (5.46 g, 19.1 mmol) was added (in 30 mL THF) and stirred for 2 h. The mixture was slowly warmed up to r.t. and quenched with sat. NH4Cl solution. The mixture was extracted with EtOAc (2×100 mL), washed with water and brine, and then dried. After removal of the solvent, the residue was purified on silica gel to give 5.3 g of the desired product. Yield: 74%.
Workup
- stirringthe reaction mixture was stirred for an additional 20 min
- stirringthe resulting solution was stirred for 20 min
- stirringstirred for 2 h
- temperatureThe mixture was slowly warmed up to r.t.
- customquenched with sat. NH4Cl solution
- extractionThe mixture was extracted with EtOAc (2×100 mL)
- washwashed with water and brine
- customdried
- customAfter removal of the solvent
- customthe residue was purified on silica gel
Sources & evidence
- ORD record
- ord-a4f835628fde4b10922b6786eb900523
- Source dataset
- uspto-grants-2009_10
- Patent number
- US07601742B2
Reaction notes
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