5-Methyl-2-thiophenecarboxaldehyde → α-Ethyl-5-methyl-2-thiophenemethanol

HRID 2293693Notes

Reaction equation

HRID 2293693 reaction equation
[CH3:1][C:2]1[S:6][C:5]([CH:7]=[O:8])=[CH:4][CH:3]=1.[CH2:9]([Mg]Br)[CH3:10]>C1COCC1>[CH2:9]([CH:7]([C:5]1[S:6][C:2]([CH3:1])=[CH:3][CH:4]=1)[OH:8])[CH3:10]

Participants

4

Reactant 2

HCID 616635-Methyl-2-thiophenecarboxaldehydeHCID 178418443HCID 178418443, compound

Product 1

HCID 19780497α-Ethyl-5-methyl-2-thiophenemethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

5-Methyl-2-thiophenecarboxaldehyde (10.0 g) is dissolved in THF and cooled to -78° C. To that solution is added ethyl magnesium bromide (1M in hexane; 80 cc) dropwise over several minutes. The cooling bath is removed and the reaction allowed to equilbrate to room temperature. The reaction is quenched by adding a saturated solution of NH4Cl. The reaction is extracted with ether, dried and evaporated to yield the title product as an almost colorless oil.

Workup

  1. customThe cooling bath is removed
  2. customto equilbrate to room temperature
  3. customThe reaction is quenched
  4. additionby adding a saturated solution of NH4Cl
  5. extractionThe reaction is extracted with ether
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-4da02d2d385c45558367a1a3bafe7b48
Source dataset
uspto-grants-1997_11
Patent number
US05686486

Reaction notes

Loading…