Sodium Iodide → HCID 70015573, compound

HRID 1603174Notes

Reaction equation

HRID 1603174 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH:11]=[CH:12][C:13]([C:15]1[CH:20]=[CH:19]C(OCOC(=O)C(C)(C)C)=[CH:17][CH:16]=1)=[O:14].[C:30]([O:36][CH2:37]I)(=[O:35])[C:31]([CH3:34])([CH3:33])[CH3:32].ClCCC(C)(C)[C:43]([O-])=[O:44].[I-].[Na+].COC1C=C(OC)C=CC=1C=CC(C1C=CC(O)=CC=1)=O.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][O:2][C:3]1[C:8]([O:44][CH3:43])=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH:11]=[CH:12][C:13]([C:15]1[CH:16]=[CH:17][C:37]([O:36][C:30](=[O:35])[C:31]([CH3:34])([CH3:33])[CH3:32])=[CH:19][CH:20]=1)=[O:14]

Participants

8

Reactant 6

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 104401Iodomethyl pivalateHCID 2888318HCID 2888318, compoundHCID 217530474-Chloro-2,2-dimethylbutanoateHCID 54257139HCID 54257139, compound

Product 1

HCID 70015573HCID 70015573, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Preparation of 2,4-dimethoxy-4'-pivaloyloxymethoxychalcone ##STR44## 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-dimethoxy4'-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. customwas prepared
  2. customThe acetonic solution was decanted from the precipitated sodium chloride
  3. waitThe combined mixtures were left for 2 days at 40° C. in a sealed flask
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a yellow gum

Sources & evidence

ORD record
ord-edc43492fb59484b99b4bf2317c02834
Source dataset
uspto-grants-1999_11
Patent number
US05985935

Reaction notes

Loading…