Dichloromethane → Ethyl 5-(1,3-dioxolan-2-yl)-2-ethylthiophene-3-carboxylate

HRID 1877254Notes

Reaction equation

HRID 1877254 reaction equation
[CH2:1]([C:3]1[S:4][C:5]([CH:13]=[O:14])=[CH:6][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:2].C[Si](C)(C)[O:17][CH2:18][CH2:19]O[Si](C)(C)C.C(Cl)Cl.FC(F)(F)S(O[Si](C)(C)C)(=O)=O>N1C=CC=CC=1>[O:14]1[CH2:19][CH2:18][O:17][CH:13]1[C:5]1[S:4][C:3]([CH2:1][CH3:2])=[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:6]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 65367Trimethylsilyl triflateHCID 818582,2,7,7-Tetramethyl-3,6-dioxa-2,7-disilaoctaneHCID 86646395Ethyl 2-ethyl-5-formylthiophene-3-carboxylate

Product 1

HCID 68509635Ethyl 5-(1,3-dioxolan-2-yl)-2-ethylthiophene-3-carboxylate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of ethyl 2-ethyl-5-formylthiophene-3-carboxylate (7.82 g) synthesized above, 1,2-bis(trimethylsiloxy)ethane (9.93 mL) and methylene chloride (80 mL) was added trimethylsilyl trifluoromethanesulfonate (661 μL) at −78° C., and the mixture was stirred for 2 hr under a nitrogen atmosphere. Pyridine (890 μL) was added to quench the reaction, and saturated aqueous sodium hydrogen carbonate solution was added. Methylene chloride was evaporated using evaporator, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over magnesium sulfate and concentrated under reduced pressure to give the title compound (9.71 g, quantitative) as a yellow oil.

Workup

  1. customto quench
  2. customthe reaction, and saturated aqueous sodium hydrogen carbonate solution
  3. additionwas added
  4. customMethylene chloride was evaporated
  5. customevaporator
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2f5900a7fcc047b6ae9a9fe8eb536f54
Source dataset
uspto-grants-2012_11
Patent number
US08309580B2

Reaction notes

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