Methyl iodide → HCID 71185284, compound
Reaction equation
[CH3:1][C:2]1[C:7]([CH3:9])([CH3:8])[C:6](=[O:10])[CH2:5][C:4]([CH3:12])([CH3:11])[C:3]=1[C:13]([O:15][CH3:16])=[O:14].[Li+].[CH3:18]C([N-]C(C)C)C.[Li]CCCC.N(C(C)C)C(C)C.CI.[NH4+].[Cl-]>C1COCC1>[CH3:1][C:2]1[C:7]([CH3:8])([CH3:9])[C:6](=[O:10])[CH:5]([CH3:18])[C:4]([CH3:11])([CH3:12])[C:3]=1[C:13]([O:15][CH3:16])=[O:14]Participants
8
Reactant 6
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
A solution of (2a) (1.0 g, 4.38 mmol) in THF (5 ml) was slowly added to a solution of LDA (freshly prepared from 3.13 ml BuLi 1.54M and 0.71 ml of iPr2NH) in THF (5 ml). The solution was stirred at −78° C. for 30 min and then a MeI (0.41 ml) was added. The mixture was stirred at −78° C. for 30 minutes then slowly warmed at room temperature After 1 hour a saturated solution of NH4Cl was added and the mixture was extracted with pentane. The organic layer was washed with saturated NH4Cl solution, bicarbonate, and brine. The collected organic layers were dried with MgSO4 and concentrated to dryness. The crude was purified by column chromatography (silicagel, cyclohexane/EtOAc 98/2). Yield 78%.
Workup
- stirringThe mixture was stirred at −78° C. for 30 minutes
- additionwas added
- extractionthe mixture was extracted with pentane
- washThe organic layer was washed with saturated NH4Cl solution, bicarbonate, and brine
- dry with materialThe collected organic layers were dried with MgSO4
- concentrationconcentrated to dryness
- customThe crude was purified by column chromatography (silicagel, cyclohexane/EtOAc 98/2)
Sources & evidence
- ORD record
- ord-2bdbc6ce2c4e4621a67711d9ded76271
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09284514B2
Reaction notes
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