Potassium Iodide → HCID 22227642, compound
Reaction equation
[C:1]([O-:4])(=[O:3])[CH3:2].[K+].[I-].[K+].Br[CH2:9][CH2:10][CH2:11][C:12]([CH2:14][CH2:15][CH2:16][C:17](=[O:22])[CH2:18][CH2:19][CH2:20]Br)=[O:13]>C(OC(=O)C)(=O)C.CCOC(C)=O>[C:1]([O:4][CH2:9][CH2:10][CH2:11][C:12]([CH2:14][CH2:15][CH2:16][C:17](=[O:22])[CH2:18][CH2:19][CH2:20][O:4][C:1](=[O:3])[CH3:2])=[O:13])(=[O:3])[CH3:2]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 25 °C
Procedure
A solution of 20.6 g potassium acetate and 3.49 g potassium iodide in 306 ml acetic anhydride was stirred and the product (VII) of Ex. 1 added. The reaction mixture was refluxed with stirring for 12-16 hrs, then cooled to 25° C. and diluted with 100 ml EtOAc. The reaction mixture was filtered, and the filtrate concentrated in vacuo. Ethyl acetate (400 ml) was added and the resultant solution was washed with 2×200 ml of 50% aq. NaHCl3. The organic layer was isolated, dried (MgSO4 an.), filtered and concentrated in vacuo. Purification by flash chromatography yielded product (VIII) in 66.3% yield as a viscous light yellow oil (93% pure).
Workup
- addition1 added
- temperatureThe reaction mixture was refluxed
- filtrationThe reaction mixture was filtered
- concentrationthe filtrate concentrated in vacuo
- additionEthyl acetate (400 ml) was added
- washthe resultant solution was washed with 2×200 ml of 50% aq. NaHCl3
- customThe organic layer was isolated
- dry with materialdried (MgSO4 an
- filtration), filtered
- concentrationconcentrated in vacuo
- customPurification by flash chromatography
Sources & evidence
- ORD record
- ord-aff82d87891d437dae1cd33949d5e21c
- Source dataset
- uspto-grants-2009_08
- Patent number
- US07572605B2
Reaction notes
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