Allyl bromide → HCID 21834427, compound
Reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([N:9]2[C:13]([CH3:14])=[CH:12][CH:11]=[C:10]2[CH3:15])[CH:3]=1.[CH2:16]([Li])[CH2:17][CH2:18]C.C(Br)C=C.[Cl-].[NH4+]>C(OCC)C.CCCCCC.C(OCC)(=O)C>[CH2:8]([C:6]1[N:5]=[C:4]([N:9]2[C:13]([CH3:14])=[CH:12][CH:11]=[C:10]2[CH3:15])[CH:3]=[C:2]([CH3:1])[CH:7]=1)[CH2:18][CH:17]=[CH2:16]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- -25 °C
Procedure
A solution of 213 mg (1.06 mmol) of 4,6-dimethyl-2-(2,5-dimethylpyrrol-1-yl)pyridine in 1.2 mL of ethyl ether was added over a 5 min period to a -25° C. solution prepared from 1.2 mL of ethyl ether and 0.75 mL (1.09 mmol) of 1.45 M n-butyllithium in hexane. The mixture was stirred for 5 min at -25° C. and then allowed to warm to -5° C. over 10 min. Allyl bromide (0.105 mL, 147 mg, 1.21 mmol) was added and the mixture was allowed to warm to 10° C. over 1 h. Saturated aqueous ammonium chloride (10 mL) was added and the mixture was extracted with 20 mL of ethyl acetate. The organic layer was washed with 10 mL of saturated aqueous sodium chloride, dried (sodium sulfate), decanted, and evaporated. Column chromatography on 20 g of silica gel eluting with 5% ethyl acetate in hexane gave 175 mg (68% yield) of 6-(3-buten-1-yl)-4-methyl-2-(2,5-dimethylpyrrol-1-yl)pyridine as a colorless oil.
Workup
- temperatureto warm to -5° C. over 10 min
- temperatureto warm to 10° C. over 1 h
- extractionthe mixture was extracted with 20 mL of ethyl acetate
- washThe organic layer was washed with 10 mL of saturated aqueous sodium chloride
- dry with materialdried (sodium sulfate)
- customdecanted
- customevaporated
Sources & evidence
- ORD record
- ord-fe83feda48d64825b4f488b475048181
- Source dataset
- uspto-grants-1999_10
- Patent number
- US05972975
Reaction notes
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