Acetic Acid → 5-Methoxy-2-(2-thienylmethylene)-1-tetralone

HRID 974780Notes

Reaction equation

HRID 974780 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7][C:8]2=[O:13].[S:14]1[CH:18]=[CH:17][CH:16]=[C:15]1[CH:19]=O.N1CCCCC1.C(O)(=O)C>>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][C:7](=[CH:19][C:15]1[S:14][CH:18]=[CH:17][CH:16]=1)[C:8]2=[O:13]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 73642-ThiophenecarboxaldehydeHCID 8082PiperidineHCID 366205-Methoxytetralone

Product 1

HCID 541268445-Methoxy-2-(2-thienylmethylene)-1-tetraloneYield 80%

Conditions

Temperature
130 °C

Procedure

A mixture of 5-methoxy-1-tetralone (1 g; 5.67 mmol), thiophene-2-carboxaldehyde (800 μl 8.51 mmol), piperidine (168 μl; 1.7 mmol) and acetic acid (97 μl; 1.7 mmol) was heated at 130° C. for 2 hours. The mixture was taken up in CH2C2 and washed in water and in a saturated aqueous solution of NaCl. The organic phase was dried over MgSO4, filtered and evaporated. The residue was purified by flash chromatography on silica gel, eluting with petroleum ether/ethyl acetate (95/5) to give 5-methoxy-2-(2-thienylmethylene)-1-tetralone (1.2 g; 80%)

Workup

  1. washwashed in water and in a saturated aqueous solution of NaCl
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by flash chromatography on silica gel
  6. washeluting with petroleum ether/ethyl acetate (95/5)

Sources & evidence

ORD record
ord-3683a43b43eb48cf852572d7483fca48
Source dataset
uspto-grants-1997_03
Patent number
US05607928

Reaction notes

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