Methyl 5-(hydroxymethyl)-3-phenylthiophene-2-carboxylate → 5-(Methoxycarbonyl)-4-phenylthiophene-2-carboxylic acid

HRID 1186717Notes

Reaction equation

HRID 1186717 reaction equation
[OH:1][CH2:2][C:3]1[S:7][C:6]([C:8]([O:10][CH3:11])=[O:9])=[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:4]=1.CC(C)=[O:20].OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[CH3:11][O:10][C:8]([C:6]1[S:7][C:3]([C:2]([OH:20])=[O:1])=[CH:4][C:5]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9]

Participants

4

Reactant 2

HCID 58121059Methyl 5-(hydroxymethyl)-3-phenylthiophene-2-carboxylateHCID 131709961Jones' reagent

Product 1

HCID 581210855-(Methoxycarbonyl)-4-phenylthiophene-2-carboxylic acidYield 91.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 169 (1.20 g, 4.83 mmol) in 30 mL of acetone was added dropwise Jones reagent (5 mL, 1.3M, 6.5 mmol) and stirred at room temperature for 1 hour. The reaction mixture was quenched with 10 mL of IPA, stirred for 10 min, filtered over a pad of Celite®. The filtrate was concentrated under vacuum, diluted in ether, washed with brine, dried over sodium sulfate, filtered, concentrated under vacuum to yield compound 174 (1.156 g, 91%) as yellow solid.

Workup

  1. customThe reaction mixture was quenched with 10 mL of IPA
  2. stirringstirred for 10 min
  3. filtrationfiltered over a pad of Celite®
  4. concentrationThe filtrate was concentrated under vacuum
  5. additiondiluted in ether
  6. washwashed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-677a9da8baa143189f32b5895e55e63e
Source dataset
uspto-grants-2014_03
Patent number
US08673911B2

Reaction notes

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