HCID 22258805, compound → HCID 22258798, compound

HRID 1611133Notes

Reaction equation

HRID 1611133 reaction equation
[CH2:1]([O:8][C:9]1[CH:13]=[CH:12][S:11][C:10]=1[C:14](N(OC)C)=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:20][Mg]Br>C1COCC1>[CH2:1]([O:8][C:9]1[CH:13]=[CH:12][S:11][C:10]=1[C:14](=[O:15])[CH3:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 22258805HCID 22258805, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 22258798HCID 22258798, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a cold (0° C.) solution of 3-(benzyloxy)-N-methoxy-N-methyl-2-thiophenecarboxamide (3.47 g, 12.50 mmol) in THF (50 mL) was added a solution of methyl-magnesium bromide in THF (1 M, 35 mL). After being stirred at 0° C. for 1 hr, the reaction mixture was quenched with saturated aqueous NH4Cl solution, diluted with water, and extracted with ethyl acetate. The separated organic phase was washed with brine, dried over Na2SO4, filtered and evaporated. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate/CH2Cl2=3/1/1) followed by recrystallization from n-hexane/ethyl acetate to give 1-[3-(benzyloxy)-2-thienyl]ethanone as a white solid (2.592 g, yield; 89%). [Starting Compound 2A]

Workup

  1. customthe reaction mixture was quenched with saturated aqueous NH4Cl solution
  2. additiondiluted with water
  3. extractionextracted with ethyl acetate
  4. washThe separated organic phase was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography on silica gel (hexane/ethyl acetate/CH2Cl2=3/1/1)
  9. customfollowed by recrystallization from n-hexane/ethyl acetate

Sources & evidence

ORD record
ord-ba126bc119f040debf1181613f6b7e06
Source dataset
uspto-grants-2006_01
Patent number
US06984649B1

Reaction notes

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