Potassium Carbonate → HCID 86647004, compound

HRID 1947780Notes

Reaction equation

HRID 1947780 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[C:9]([CH:10]2[CH:14](I)[CH2:13][O:12][O:11]2)=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:17](=O)([O-])[O-].[K+].[K+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3](=[O:16])[C:4]1[C:9]([CH:10]2[CH:14]([CH3:17])[CH2:13][O:12][O:11]2)=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 86647002HCID 86647002, compound

Product 1

HCID 86647004HCID 86647004, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
105 °C

Procedure

A suspension of 5-iodo-2,3-dioxolanebenzoic acid methyl ester (0.1 g, 0.32 mmol), potassium carbonate (0.048 g, 0.35 mmol), tetrakis(triphenylphosphine)palladium (1 mol %) and trimethylboraxine (0.089 ml, 0.64 mmol) in 1,4-dioxane (5 ml) is stirred under nitrogen at 105° C. for 10 hours. Solvent is removed and the residue is taken in ethyl acetate (50 ml). This mixture is washed with water (30 ml), dried with sodium sulphate and evaporated. Purification by chromatography (ethyl acetate/hexane 5:95) gives 5-methyl-2,3-dioxolanebenzoic acid methyl ester; GC/MS: 194 (M+1)+.

Workup

  1. customSolvent is removed
  2. washThis mixture is washed with water (30 ml)
  3. dry with materialdried with sodium sulphate
  4. customevaporated
  5. customPurification by chromatography (ethyl acetate/hexane 5:95)

Sources & evidence

ORD record
ord-3c61eeb359df4d2da229d87afd04d399
Source dataset
uspto-grants-2013_03
Patent number
US08399490B2

Reaction notes

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