Water → HCID 19261483, compound

HRID 617205Notes

Reaction equation

HRID 617205 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([O:13][CH3:14])=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9])=[O:2].C[Si]([C:19]#[N:20])(C)C.O>C(Cl)Cl.[I-].[Zn+2].[I-]>[C:19]([CH:1]([C:3]1[CH:4]=[CH:5][C:6]([O:13][CH3:14])=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9])[OH:2])#[N:20]

Participants

6

Reactant 3

HCID 962WaterHCID 82115Trimethylsilyl cyanideHCID 10856352Methyl 5-formyl-2-methoxybenzoate

Product 1

HCID 19261483HCID 19261483, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of methyl 5-formyl-2-methoxybenzoate (55.61 g) and zinc iodide (960 mg) in methylene chloride (560 ml) was added trimethylsilyl cyanide (48 ml) in an argon atmosphere under ice cooling and stirring, and the mixture was stirred for 6.5 hours as it was. The reaction mixture was poured into water and methylene chloride layer was separated. After washing with water, it was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was dissolved into 1,3-dioxolane (400 ml) and 2 N hydrochloric acid (200 ml) was added, which was allowed to stand for 1.5 hours at room temperature. The reaction liquor was poured into water and extracted with ethyl acetate. This was washed with water, brine and then dried over anhydrous sodium sulfate. This was concentrated to about 200 ml under reduced pressure and the crystals deposited were collected by filtration and dried to obtain 39.41 g (62%) of aimed compound as pale yellow crystals.

Workup

  1. stirringthe mixture was stirred for 6.5 hours as it
  2. customwas separated
  3. washAfter washing with water, it
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe residue was dissolved into 1,3-dioxolane (400 ml) and 2 N hydrochloric acid (200 ml)
  7. additionwas added
  8. additionThe reaction liquor was poured into water
  9. extractionextracted with ethyl acetate
  10. washThis was washed with water, brine
  11. dry with materialdried over anhydrous sodium sulfate
  12. concentrationThis was concentrated to about 200 ml under reduced pressure
  13. filtrationthe crystals deposited were collected by filtration
  14. customdried

Sources & evidence

ORD record
ord-82ea2f2f3e1d419cb222dabfac0c4c6d
Source dataset
uspto-grants-1999_09
Patent number
US05948803

Reaction notes

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