Metaperiodic acid → 3-Cyano-thiophene-2,5-dicarboxylic acid 2-methyl ester

HRID 1952649Notes

Reaction equation

HRID 1952649 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH2:12][OH:13])=[CH:8][C:9]=1[C:10]#[N:11])=[O:4].I(O)(=O)(=O)=[O:15]>CC#N.CCOC(C)=O.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:12]([OH:15])=[O:13])=[CH:8][C:9]=1[C:10]#[N:11])=[O:4]

Participants

6

Reactant 2

HCID 65185Metaperiodic acidHCID 682266643-Cyano-5-hydroxymethyl-thiophene-2-carboxylic acid methyl ester

Product 1

HCID 682271093-Cyano-thiophene-2,5-dicarboxylic acid 2-methyl esterYield 90.5%

Reagents, catalysts & solvents 3

HCID 178418287HCID 178418287, compoundCatalystHCID 6342AcetonitrileSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-Cyano-5-hydroxymethyl-thiophene-2-carboxylic acid methyl ester (0.1342 g, 0.68 mmol) and Periodic Acid (0.34 g, 1.50 mmol) in MeCN (9.5 ml) was stirred for 30 min. A solution of PCC (0.010 g, 0.015 mmol) in MeCN (0.5 ml) was added. After 1 h, the reaction mixture was diluted with EtOAc (50 ml), washed with sodium sulfite, brine, dried over sodium sulfate, filtered and evaporated. Isolate 0.13 g (90%) of beige solid.

Workup

  1. waitAfter 1 h
  2. washwashed with sodium sulfite, brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-cba297de66d94cd1b9b292be0225f19b
Source dataset
uspto-grants-2013_03
Patent number
US08404859B2

Reaction notes

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