3-Benzyloxy-5-(methylsulfonyl)-2-thiophenecarboxylic Acid → 4-Benzyloxy-2-(methylsulfonyl)thiophene

HRID 1953965Notes

Reaction equation

HRID 1953965 reaction equation
[CH2:1]([O:8][C:9]1[CH:13]=[C:12]([S:14]([CH3:17])(=[O:16])=[O:15])[S:11][C:10]=1C(O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>N1C2C(=CC=CC=2)C=CC=1>[CH2:1]([O:8][C:9]1[CH:13]=[C:12]([S:14]([CH3:17])(=[O:16])=[O:15])[S:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 154771003-Benzyloxy-5-(methylsulfonyl)-2-thiophenecarboxylic Acid

Product 1

HCID 154771014-Benzyloxy-2-(methylsulfonyl)thiopheneYield 86%

Reagents, catalysts & solvents 1

HCID 7047QuinolineSolvent

Conditions

Temperature
165 °C

Procedure

A solution of 3-benzyloxy-5-(methylsulfonyl)-2-thiopenecarboxylic acid (13.6 g, 43.6 mmol) in 50 ml quinoline is treated with Cu powder (4.15 g, 65.4 mmol) at room temperature, heated to 165° C. for 15 minutes, cooled to room temperature and filtered. (The filtercake is washed with water.) The combined filtrate is acidified to pH 1 with 6N HCl and filtered. This filtercake is washed with water and dried to afford the title product as a dark grey powder, 10.1 g (86% yield), mp 108-109° C., identified by 1HNMR, 13CNMR and mass spectral analyses.

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. wash(The filtercake is washed with water
  4. filtrationfiltered
  5. washThis filtercake is washed with water
  6. customdried

Sources & evidence

ORD record
ord-93b5e80c704445278fcad4cb2e49b352
Source dataset
uspto-grants-2000_09
Patent number
US06121202

Reaction notes

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