Iodine → HCID 19885922, compound

HRID 654919Notes

Reaction equation

HRID 654919 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.BrCCCC1C=CC=CC=1.[Mg].II.[O:25]1[CH:29]=[CH:28][C:27]([CH:30]=[O:31])=[CH:26]1.S(=O)(=O)(O)O>C(OCC)C>[OH:31][CH:30]([C:27]1[CH:28]=[CH:29][O:25][CH:26]=1)[CH2:9][CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 6

HCID 807IodineHCID 1118Sulfuric AcidHCID 103513-FuraldehydeHCID 12503(3-Bromopropyl)benzeneHCID 5462224MagnesiumHCID 178418471HCID 178418471, compound

Product 1

HCID 19885922HCID 19885922, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred solution of 3-phenylpropyl magnesium bromide (4.5 ml of a 2.73M solution in ethyl ether, 12.3 mmol, generated from 1-bromo-3-phenylpropane and magnesium and initiated with iodine) at 0° under argon, was added dropwise 3-furaldehyde (1.08 g., 11.2 mmol) in 5 ml ethyl ether. This solution was allowed to warm to room temperature, stirred for 20 minutes, and then poured over crushed ice containing several drops of concentrated sulfuric acid. The resulting mixture was partitioned between ethyl ether and 5% sodium bisulfite. The organic portion was washed with 5% sodium bicarbonate solution, water, saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to give an oil. This material was further purified by flash chromatography (silica, 20% ethyl acetate/hexane) to give the desired alcohol.

Workup

  1. customat 0°
  2. additionpoured
  3. customThe resulting mixture was partitioned between ethyl ether and 5% sodium bisulfite
  4. washThe organic portion was washed with 5% sodium bicarbonate solution, water, saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give an oil
  9. customThis material was further purified by flash chromatography (silica, 20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-078415d80342456ab2945148936f90e0
Source dataset
uspto-grants-1992_07
Patent number
US05134128

Reaction notes

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