Iodine → (3r,5r)-3-Heptyl-5-iodomethyl-dihydrofuran-2-one

HRID 1955428Notes

Reaction equation

HRID 1955428 reaction equation
[CH2:1]([C@H:8]([CH2:12][CH:13]=[CH2:14])[C:9]([OH:11])=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[I:15]I>C1COCC1.O.CCOCC>[CH2:1]([C@@H:8]1[CH2:12][C@H:13]([CH2:14][I:15])[O:10][C:9]1=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 2

HCID 807IodineHCID 11041739(2R)-2-Heptyl-pent-4-enoic acid

Product 1

HCID 10903418(3r,5r)-3-Heptyl-5-iodomethyl-dihydrofuran-2-oneYield 71.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of 7.14 g (0.036 mol) of the product of Example 5 in 750 mL of THF/H2O (2:1), cooled to 0 degrees, was added 7.22 g (0.072 mol) of KHCO3 followed by 11.97 g (0.072 mol) of KI and then 18.30 g (0.072 mol) of iodine. The reaction was allowed to warm to room temperature and stirred for 18 h. The resulting mixture was diluted with ether and the organic layer was washed with aqueous sodium bisulfite solution, H2O and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:10) to provide 8.30 g (71%) of the title compound and 3.36 g (29%) of the corresponding iodo-trans lactone as white solids. CI Mass Spec: 325.3 (M+H).

Workup

  1. washthe organic layer was washed with aqueous sodium bisulfite solution, H2O and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:10)

Sources & evidence

ORD record
ord-58b1b1de57d1419c9534eed28c422761
Source dataset
uspto-grants-2000_09
Patent number
US06124502

Reaction notes

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