Reaction equation
[CH3:1][C:2](=[CH:4][CH2:5][CH2:6][C@@H:7]([CH2:9][CH2:10]O)[CH3:8])[CH3:3].N1C=CN=C1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:36]I>C1COCC1.CCCCCC>[I:36][CH2:10][CH2:9][C@@H:7]([CH3:8])[CH2:6][CH2:5][CH:4]=[C:2]([CH3:3])[CH3:1]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 3.12 g (20.0 mmol) of (S)-(-)-β-citronellol (purchased from Aldrich Chem. Co.) and 2.72 g (40.0 mmol) of imidazole in 50 mL of THF at 0° C. was treated with 5.0 g (19.5 mmol) of triphenylphosphine followed by 4.83 g (19.0 mmol) of I2 in 25 mL of THF dropwise over 20 minutes. The reaction mixture was stirred for 1.0 hour and was diluted with hexane. The organic mixture was washed with aqueous Na2SO3, brine, dried (Na2SO4) and evaporated to provide a crude white slurry. The slurry was purified by flash chromatography (300 g of silica gel) eluting with hexane to provide 4.00 g (79%) of title iodide as a colorless oil.
Workup
- washThe organic mixture was washed with aqueous Na2SO3, brine
- dry with materialdried (Na2SO4)
- customevaporated
- customto provide a crude white slurry
- customThe slurry was purified by flash chromatography (300 g of silica gel)
- washeluting with hexane
Sources & evidence
- ORD record
- ord-0824be1d0c9b43e890ce4acc0d6c7a8c
- Source dataset
- uspto-grants-1992_10
- Patent number
- US05157027
Linked notes
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