Sodium Iodide → HCID 585393, compound

HRID 325126Notes

Reaction equation

[I-].[Na+].C[Si](C)(C)Cl.[C:8]([O:14][CH2:15][CH3:16])(=[O:13])[CH2:9][C:10]([CH3:12])=[O:11].[CH:17]1[C:22]([CH:23]=O)=[CH:21][C:20]2[O:25][CH2:26][O:27][C:19]=2[CH:18]=1>C(#N)C.CCOCC.O>[CH2:15]([O:14][C:8](=[O:13])[CH:9]([CH2:23][C:22]1[CH:17]=[CH:18][C:19]2[O:27][CH2:26][O:25][C:20]=2[CH:21]=1)[C:10](=[O:11])[CH3:12])[CH3:16]

Participants

Conditions

Temperature: 2.5 °C

Procedure

To a solution of 117.2 g sodium iodide in 700 ml of acetonitrile, first 85.9 g trimethylchlorosilane and then 20.56 g ethyl acetoacetate were dropped in at room temperature. After cooling down to 0-5° C., a solution of 23.65 g Piperonal in 50 ml of acetonitrile was dropped in. Then the mixture was stirred at room temperature for 5 hours and then at 60° C. overnight. After the mixture was cooled down to room temperature it was diluted with ether and water. The organic phase was separated and washed with saturated sodium thiosulfate until the color of the iodine was gone. Then the organic phase was washed with water, dried, filtered and evaporated to dryness. The resulting dark oil was purified by chromatography to yield 13.7 g of a yellow oil.

Workup

customat 60° C.
customovernight
temperatureAfter the mixture was cooled down to room temperature it
customThe organic phase was separated
washwashed with saturated sodium thiosulfate until the color of the iodine
washThen the organic phase was washed with water
customdried
filtrationfiltered
customevaporated to dryness
customThe resulting dark oil was purified by chromatography

Sources & evidence

ORD record: ord-0e87609263fe4714862e7a1328b18f96
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06222062B1

Reaction notes

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