HCID 22473796, compound → HCID 22474287, compound

HRID 2183663Notes

Reaction equation

HRID 2183663 reaction equation
[CH2:1]([Mg]Br)[CH3:2].CON(C)[C:8]([C:10]1[S:14][C:13]2[C:15]([O:19][CH3:20])=[CH:16][CH:17]=[CH:18][C:12]=2[CH:11]=1)=[O:9]>O1CCCC1>[CH3:20][O:19][C:15]1[C:13]2[S:14][C:10]([C:8](=[O:9])[CH2:1][CH3:2])=[CH:11][C:12]=2[CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 22473796HCID 22473796, compoundHCID 178418443HCID 178418443, compound2×

Product 1

HCID 22474287HCID 22474287, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethylmagnesium bromide (1M solution in tetrahydrofuran; 6.4 ml) was added to a solution of N,7-dimethoxy-N-methylbenzo[b]thiophene-2-carboxamide (1.5 g) in tetrahydrofuran, then the mixture was stirred at ambient temperature for 1 hour and at reflux temperature for 1 hour. Further ethylmagnesium bromide (1M solution in tetrahydrofuran; 6.4 ml) was added, the mixture was stirred at ambient temperature for 1 hour and at reflux temperature for 2.5 hour, then it was cooled to ambient temperature and quenched by the addition of 5M hydrochloric acid (10 ml) and water (150 ml). The product was extracted into dichloromethane (3×60 ml), then the combined extracts were dried (MgSO4) and the solvents were removed in vacuo. The residue was purified by flash chromatography over silica using dichloromethane followed by a 99:1 mixture of dichloromethane and methanol as eluants. Appropriate fractions were combined, and the solvents were removed in vacuo to give 1-(7-methoxybenzo[b]thiophen-2-yl)propan-1-one (0.7 g) as an oil which was used without further purification.

Workup

  1. temperatureat reflux temperature for 1 hour
  2. stirringthe mixture was stirred at ambient temperature for 1 hour
  3. temperatureat reflux temperature for 2.5 hour
  4. temperatureit was cooled to ambient temperature
  5. customquenched by the addition of 5M hydrochloric acid (10 ml) and water (150 ml)
  6. extractionThe product was extracted into dichloromethane (3×60 ml)
  7. dry with materialthe combined extracts were dried (MgSO4)
  8. customthe solvents were removed in vacuo
  9. customThe residue was purified by flash chromatography over silica
  10. additionfollowed by a 99:1 mixture of dichloromethane and methanol as eluants
  11. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-cfb2c8a135534d619de7ea9020f0e1fb
Source dataset
uspto-grants-2005_05
Patent number
US06900216B2

Reaction notes

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