Methane → HCID 20377675, compound

HRID 1703482Notes

Reaction equation

HRID 1703482 reaction equation
C([C:4]1[S:8][C:7]2[S:9][C:10]([C:12]([C:14]3[CH:15]=[C:16]([CH:20]([CH3:24])[C:21]([OH:23])=[O:22])[CH:17]=[CH:18][CH:19]=3)=[O:13])=[CH:11][C:6]=2[CH:5]=1)(O)=O.C>C1(OC2C=CC=CC=2)C=CC=CC=1.C(Cl)Cl.[Cu]>[S:9]1[C:7]2[S:8][CH:4]=[CH:5][C:6]=2[CH:11]=[C:10]1[C:12]([C:14]1[CH:15]=[C:16]([CH:20]([CH3:24])[C:21]([OH:23])=[O:22])[CH:17]=[CH:18][CH:19]=1)=[O:13]

Participants

6

Reactant 2

HCID 297MethaneHCID 20377674HCID 20377674, compound

Product 1

HCID 20377675HCID 20377675, compoundYield 61%

Reagents, catalysts & solvents 3

HCID 23978CopperCatalyst2×HCID 6344DichloromethaneSolventHCID 7583Diphenyl EtherSolvent

Conditions

Temperature
250 °C

Procedure

2-{3-(5-Carboxy-thieno[2,3-b]thien-2-yl)carbonyl-phenyl}propionic acid (14 g), copper powder (1.5 g) and copper turnings (1.5 g) are suspended in diphenyl ether (60 cc) and heated at 250° C. for 30 minutes. After cooling, the reaction mixture is diluted with methylene chloride (100 cc), decolourizing charcoal (1 g) is added and the mixture is filtered. The filtrate is extracted three times with a 10% (w/v) aqueous solution of sodium carbonate (total 150 cc), and then washed twice with distilled water (total 100 cc). The combined aqueous phases are acidified to pH 1 by the addition of 12N concentrated hydrochloric acid and extracted four times with methylene chloride (total 200 cc). The combined methylene chloride solutions are washed three times with distilled water (total 90 cc), dried over anhydrous sodium sulphate and evaporated. Crude 2-{3-(thieno[2,3-b]thien-2-yl)carbonyl-phenyl}propionic acid (7.5 g) in the form of an oil is thus obtained.

Workup

  1. temperatureAfter cooling
  2. additionis added
  3. filtrationthe mixture is filtered
  4. extractionThe filtrate is extracted three times with a 10% (w/v) aqueous solution of sodium carbonate (total 150 cc)
  5. washwashed twice with distilled water (total 100 cc)
  6. additionThe combined aqueous phases are acidified to pH 1 by the addition of 12N concentrated hydrochloric acid
  7. extractionextracted four times with methylene chloride (total 200 cc)
  8. washThe combined methylene chloride solutions are washed three times with distilled water (total 90 cc)
  9. dry with materialdried over anhydrous sodium sulphate
  10. customevaporated

Sources & evidence

ORD record
ord-e94d5206a8da4dc5aff7c5144cd4359b
Source dataset
uspto-grants-1978_11
Patent number
US04124596

Reaction notes

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