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

HRID 1275405Notes

Reaction equation

HRID 1275405 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 warn 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. customto warn to room temperature
  2. washthe organic layer was washed with aqueous sodium bisulfite solution, H2O and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:10)

Sources & evidence

ORD record
ord-666ce470accf447aa100ca4ee1f1f405
Source dataset
uspto-grants-2000_12
Patent number
US06160132

Reaction notes

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