Acetic Acid → HCID 54371093, compound

HRID 974779Notes

Reaction equation

HRID 974779 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][CH2:6][C:7]2=[O:12].[S:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[CH:18]=O.N1CCCCC1.C(O)(=O)C>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][C:6](=[CH:18][C:14]1[S:13][CH:17]=[CH:16][CH:15]=1)[C:7]2=[O:12]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 73642-ThiophenecarboxaldehydeHCID 8082PiperidineHCID 45474914-methoxy-2,3-dihydro-1H-inden-1-one

Product 1

HCID 54371093HCID 54371093, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
130 °C

Procedure

To 4-methoxy-1-indanone (0.1 g; 0.62 mmol) were added thiophene-2-carboxaldehyde (87.5 μl ; 0.93 mmol), piperidine (18.5 μl ; 0.18 mmol) and acetic acid (10.7 μl ; 0.18 mmol). After heating at 130° C. for 90 minutes the mixture was taken up in CH2Cl2, washed with water and purified by flash chromatography, eluting with petroleum ether/ethyl acetate (95/5) to give 4-methoxy-2-(2-thienylmethylene)-1-indanone (140 mg; 90%).

Workup

  1. washwashed with water
  2. custompurified by flash chromatography
  3. washeluting with petroleum ether/ethyl acetate (95/5)

Sources & evidence

ORD record
ord-5d261c75f25f4b1a9cc61a7ea2abca42
Source dataset
uspto-grants-1997_03
Patent number
US05607928

Reaction notes

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