Sodium Bicarbonate → 3-Chloro-5-hydroxymethyl-thiophene-2-carboxylic acid methyl ester

HRID 1952595Notes

Reaction equation

HRID 1952595 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH2:11]Br)=[CH:8][C:9]=1[Cl:10])=[O:4].C([O-])(O)=[O:14].[Na+]>CS(C)=O.O>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH2:11][OH:14])=[CH:8][C:9]=1[Cl:10])=[O:4]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 682268765-Bromomethyl-3-chloro-thiophene-2-carboxylic acid methyl ester

Product 1

HCID 682265743-Chloro-5-hydroxymethyl-thiophene-2-carboxylic acid methyl esterYield 45%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of 5-Bromomethyl-3-chloro-thiophene-2-carboxylic acid methyl ester (3.8 g, 14.1 mmol) and NaHCO3 (20 g, 238 mmol) in DMSO (100 ml) was heated at 115° C. for 4 h. The reaction mixture was cooled. The reaction mixture was diluted with water and extracted with DCM (3×100 mL), washed with brine, dried over sodium sulfate, filtered and evaporated. The residue was purified by column (0-30% EtOAc in hexane) to give 1.30 g (45%) product.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with DCM (3×100 mL)
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column (0-30% EtOAc in hexane)

Sources & evidence

ORD record
ord-efabfd0e4e9b4697b8a03a0a0bc5b05f
Source dataset
uspto-grants-2013_03
Patent number
US08404859B2

Reaction notes

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