Methyl iodide → HCID 59568838, compound
Reaction equation
[H-].[Na+].[O:3]1[CH2:7][CH2:6][O:5][CH:4]1[CH2:8][CH2:9][CH:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18])[OH:11].[CH3:19]I>C1COCC1>[CH3:19][O:11][CH:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18])[CH2:9][CH2:8][CH:4]1[O:5][CH2:6][CH2:7][O:3]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a suspension of NaH (468 mg of a 60% dispersion in mineral oil, 11.7 mmol) in 35 mL THF was slowly added 3-[1,3]Dioxolan-2-yl-1-o-tolyl-propan-1-ol (290.0 mg, 1.3 mmol) as a solution in 15 mL THF at room temperature followed by the dropwise addition of methyl iodide (624 L, 1.4 g, 9.6 mmol). The mixture was stirred for 3 h at room temperature before being quenched by the careful addition of saturated aqueous NH4Cl (40 mL). The resulting mixture was extracted with ethyl acetate (3×30 mL) and the combined organic layers washed with brine (2×20 mL) and dried over sodium sulfate. The solvents were evaporated under reduced pressure and the product isolated by flash column chromatography eluting with 0% to 30% ethyl acetate/hexane to give 285 mg of the title compounds as an oil.
Workup
- customat room temperature
- custombefore being quenched by the careful addition of saturated aqueous NH4Cl (40 mL)
- extractionThe resulting mixture was extracted with ethyl acetate (3×30 mL)
- washthe combined organic layers washed with brine (2×20 mL)
- dry with materialdried over sodium sulfate
- customThe solvents were evaporated under reduced pressure
- customthe product isolated by flash column chromatography
- washeluting with 0% to 30% ethyl acetate/hexane
Sources & evidence
- ORD record
- ord-51082e58007c4c6a807aad4c8d1e7476
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08119692B2
Reaction notes
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