Diiodomethane → 9-Oxa-bicyclo[15.1.0]octadecan-8-one

HRID 548523Notes

Reaction equation

HRID 548523 reaction equation
[CH2:1](I)I.[O:4]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH:12]=[CH:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:5]1=[O:21]>CCOCC>[CH:12]12[CH2:1][CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:4][C:5](=[O:21])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]2

Participants

4

Reactant 2

HCID 6346DiiodomethaneHCID 312671-Oxacycloheptadec-8-en-2-one

Product 1

HCID 231495529-Oxa-bicyclo[15.1.0]octadecan-8-one

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a dry 500 ml multi-neck round bottom flask fitted with an air stirrer, nitrogen inlet condenser and an addition funnel 8 g of ZnCu, 26 g of CH2I2, 100 ml of Et2O and 2 crystals of 12, were added and stirred. 12 g of oxacycloheptadec-8-en-2-one were added to the mixture and the mixture was heated to reflux. In 4 hours, first sample was taken at 35° C. The mixture was left to age overnight. Next morning, the mixture was quenched with saturated NH4Cl, aqueous layer separated and the organic layer washed with NaHCO3. The organic layer was then dried over anhydrous MgSO4. The gas chromatography test indicated that 8.1% of the starting alkene lactone converted to the cyclopropanated lactone.

Workup

  1. additionwere added
  2. temperaturethe mixture was heated to reflux
  3. customwas taken at 35° C
  4. waitThe mixture was left to age overnight
  5. customNext morning, the mixture was quenched with saturated NH4Cl, aqueous layer
  6. customseparated
  7. washthe organic layer washed with NaHCO3
  8. dry with materialThe organic layer was then dried over anhydrous MgSO4

Sources & evidence

ORD record
ord-03143e8165ce41638165ad1ee1fd9b1b
Source dataset
uspto-grants-2011_05
Patent number
US07943560B2

Reaction notes

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