HCID 58629740, compound → HCID 58629777, compound

HRID 423261Notes

Reaction equation

HRID 423261 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH2:13][O:14][CH3:15])=[C:6](I)[CH:5]=1.[CH3:18][Zn]C.C1COCC1>C1COCC1.C(OCC)(=O)C.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:17])[C:4]1[CH:5]=[C:6]([CH3:18])[C:7]([O:12][CH2:13][O:14][CH3:15])=[C:8]([O:10][CH3:11])[CH:9]=1

Participants

6

Reactant 2

HCID 58629740HCID 58629740, compoundHCID 178420677HCID 178420677, compound

Product 1

HCID 58629777HCID 58629777, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-iodo-5-methoxy-4-methoxymethoxybenzoic acid methyl ester (700 mg) in THF (7 mL) were added tetrakis(triphenylphosphine)palladium(0) (115 mg) and 2M dimethylzinc/THF solution (1.20 mL), and the mixture was stirred at 80° C. for 30 minutes. The reaction solution was diluted with ethyl acetate, washed with 1N hydrochloric acid, water, and saturated brine, dried over anhydrous sodium sulfate, and concentrated in vacuo to give the title compound (767 mg) as a crude purified product of pale yellow oil.

Workup

  1. washwashed with 1N hydrochloric acid, water, and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7b12c58f793d4e59befb3ec9ed4bc0ea
Source dataset
uspto-grants-2012_01
Patent number
US08101774B2

Reaction notes

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