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

HRID 1952596Notes

Reaction equation

HRID 1952596 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH2:11][OH:12])=[CH:8][C:9]=1[Cl:10])=[O:4].I(O)(=O)(=O)=[O:14]>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:11]([OH:14])=[O:12])=[CH:8][C:9]=1[Cl:10])=[O:4]

Participants

6

Reactant 2

HCID 65185Metaperiodic acidHCID 682265743-Chloro-5-hydroxymethyl-thiophene-2-carboxylic acid methyl ester

Product 1

HCID 682266273-Chloro-thiophene-2,5-dicarboxylic acid 2-methyl esterYield 86.5%

Reagents, catalysts & solvents 3

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

Procedure

A mixture of 3-chloro-5-hydroxymethyl-thiophene-2-carboxylic acid methyl ester (1.3 g, 6.29 mmol) and Periodic Acid (3.15 g, 13.84 mmol) in MeCN (40 ml) was stirred for 30 min. A solution of PCC (0.027 g, 0.13 mmol) in MeCN (2 ml) was added. After 5 h, the reaction mixture was diluted with EtOAc (250 ml), washed with sodium sulfite, brine, dried over sodium sulfate, filtered and evaporated. Isolate 1.20 g (86%) of yellow solid product.

Workup

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

Sources & evidence

ORD record
ord-6510020dc4b34ec485fafb8414a092cf
Source dataset
uspto-grants-2013_03
Patent number
US08404859B2

Reaction notes

Loading…