Sodium Iodide → HCID 70015573, compound

HRID 394971Notes

Reaction equation

HRID 394971 reaction equation
ClC[CH2:3][C:4]([CH3:9])([CH3:8])[C:5]([O-:7])=[O:6].[I-:10].[Na+].[CH3:12][O:13][C:14]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=1[CH:22]=[CH:23][C:24]([C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=1)=[O:25].[C:33](=O)([O-])[O-:34].[K+].[K+]>CC(C)=O>[C:5]([O:7][CH2:12][I:10])(=[O:6])[C:4]([CH3:9])([CH3:8])[CH3:3].[CH3:12][O:13][C:14]1[C:19]([O:34][CH3:33])=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=1[CH:22]=[CH:23][C:24]([C:26]1[CH:27]=[CH:28][C:29]([O:32][C:5](=[O:6])[C:4]([CH3:9])([CH3:8])[CH3:3])=[CH:30][CH:31]=1)=[O:25]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 2888318HCID 2888318, compoundHCID 217530474-Chloro-2,2-dimethylbutanoate

Product 2

HCID 104401Iodomethyl pivalateHCID 70015573HCID 70015573, compoundYield 120.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

An acetonic solution of iodomethyl pivalate was prepared by allowing 0.29 g (2.1 mmol) of chloromethylpivalate to react for 30 min with 0.15 g (5.7 mmol) of sodium iodide dissolved in 10 ml of dry acetone. The acetonic solution was decanted from the precipitated sodium chloride and added to a suspension of 0.57 g (2 mmol) of 2,4-dimethoxy-4′-hydroxychalcone and 0.5 g (3.7 mmol) of potassium carbonate, which had previously been stirred under argon atmosphere for 30 min. The combined mixtures were left for 2 days at 40° C. in a sealed flask, filtered, and concentrated in vacuo to give a yellow gum, from which 0.48 g (60%) of 2,4-dimethoxy-4′-pivaloyloxy-methoxychalcone was isolated as a yellow oil by column chromatography over silica gel 60 (Merck 0.063-0.200 mm, 80 g) using petroleum ether-ethyl acetate (9:1, 1500 ml) as an eluent. The compound crystallized upon standing, m.p. 98-99° C. (methanol).

Workup

  1. customThe acetonic solution was decanted from the precipitated sodium chloride
  2. waitThe combined mixtures were left for 2 days at 40° C. in a sealed flask
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give a yellow gum

Sources & evidence

ORD record
ord-a9407ed0942849c78d2542620cc3fe90
Source dataset
uspto-grants-2003_08
Patent number
US06603046B1

Reaction notes

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