Sodium Iodide → 1-(Tert-butyldimethylsilyl)oxy-3-iodocyclohexane
Reaction equation
[Si:1]([O:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH:11](OS(C)(=O)=O)[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[I-:20].[Na+].C(OCC)(=O)C.CCCCCC>CN(C)C=O>[Si:1]([O:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH:11]([I:20])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]Participants
Procedure
A solution of 3-(tert-butyldimethylsilyl)oxy-1-(methylsulfonyloxy)cyclohexane (15.9 g) and sodium iodide (8.5 g) in N,N-dimethylformamide (80 ml) was heated at 100° C. for 3 hours with stirring. After cooled to ambient temperature, a reaction mixture was poured into a mixture of ethyl acetate (250 ml) and n-hexane (150 ml), and insoluble material was removed by filtration. Mother liquor was washed in turn with water (100 ml×3), 5% sodium thiosulfate in water (50 ml), and saturated sodium chloride in water (100 ml×2), and dried over magnesium sulfate. Evaporation of the solvent gave a residue, which was chromatographed on silica gel (300 ml) eluting with 10% ethyl acetate in n-hexane to give 3-(tert-butyldimethylsilyl)oxy-1-iodocyclohexane (cis and trans mixture).
Workup
- customwas removed by filtration
- washMother liquor was washed in turn with water (100 ml×3), 5% sodium thiosulfate in water (50 ml), and saturated sodium chloride in water (100 ml×2)
- dry with materialdried over magnesium sulfate
- customEvaporation of the solvent
- customgave a residue, which
- customwas chromatographed on silica gel (300 ml)
- washeluting with 10% ethyl acetate in n-hexane
Sources & evidence
- ORD record
- ord-bb18c196a2854166927a4c720355f97f
- Source dataset
- uspto-grants-2002_03
- Patent number
- US06355640B1
Reaction notes
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