Diethyl Ether → HCID 20285737, compound

HRID 1764586Notes

Reaction equation

HRID 1764586 reaction equation
Br[C:2]1[C:3]([CH3:11])=[C:4]([CH2:8][O:9][CH3:10])[S:5][C:6]=1[CH3:7].[CH2:12]([O:14]CC)C.C([Li])CCC>CN(C)C=O>[CH3:7][C:6]1[S:5][C:4]([CH2:8][O:9][CH3:10])=[C:3]([CH3:11])[C:2]=1[CH:12]=[O:14]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 20285728HCID 20285728, compoundHCID 178418339Butyllithium

Product 1

HCID 20285737HCID 20285737, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-70 °C

Procedure

15.5 G. of 4-bromo-3,5-dimethyl-2-methoxymethylthiophene was dissolved in 200 ml. of anhydrous ethyl ether under argon. The resulting solution was cooled to -70° C. and 22 ml. of a 2.4 M solution of n-butyl lithium was slowly added. The reaction mixture was warmed to -30° C. for 10 minutes and then cooled to -70° C. 7.3 G. of dimethylformamide was slowly added and the reaction was warmed to room temperature for 14 hours. The resulting reaction mixture was poured into ice water, stirred for 15 minutes and extracted with ethyl ether. The combined ether extracts were washed with a solution of 5% sodium carbonate, a saturated solution of sodium chloride, dried over sodium sulfate, filtered and evaporated to yield 2,4-dimethyl-5-methoxymethylthiophene-3-carboxaldehyde.

Workup

  1. temperatureThe reaction mixture was warmed to -30° C. for 10 minutes
  2. temperaturecooled to -70° C
  3. temperaturethe reaction was warmed to room temperature for 14 hours
  4. customThe resulting reaction mixture
  5. extractionextracted with ethyl ether
  6. washThe combined ether extracts were washed with a solution of 5% sodium carbonate
  7. dry with materiala saturated solution of sodium chloride, dried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-17d50f30abfb451a85aff206f84a08a5
Source dataset
uspto-grants-1978_09
Patent number
US04116975

Reaction notes

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