2-tert-Butylthiophene → 5-(Tert-butyl)thiophene-2-carbaldehyde

HRID 1252462Notes

Reaction equation

HRID 1252462 reaction equation
P(Cl)(Cl)(Cl)=O.CN([CH:14]=[O:15])C1C=CC=CC=1.[C:16]([C:20]1[S:21][CH:22]=[CH:23][CH:24]=1)([CH3:19])([CH3:18])[CH3:17].C(=O)(O)[O-].[Na+]>>[C:16]([C:20]1[S:21][C:22]([CH:14]=[O:15])=[CH:23][CH:24]=1)([CH3:19])([CH3:18])[CH3:17]

Participants

5

Reactant 4

HCID 155282-tert-ButylthiopheneHCID 24813Phosphorus oxychlorideHCID 66737N-MethylformanilideHCID 516892Sodium Bicarbonate

Product 1

HCID 149549895-(Tert-butyl)thiophene-2-carbaldehydeYield 87.3%

Conditions

Temperature
0 °C

Procedure

Phosphorus oxychloride (24.04 g, 0.157 mol) was added dropwise to N-methylformanilide (21.24 g, 0.157 mol) and a yellow solid was produced. This was cooled to 0° C. for 1/2 hour, then 2-t-butylthiophene (20 g, 0.143 mol) was added dropwise and the mixture stirred at room temperature for 3 hours. The mixture was poured into ice/water, neutralised with sodium bicarbonate and extracted into diethyl ether. The ethereal extracts were washed with water, dried over anhydrous sodium sulphate and the solvent removed to give a brown liquid. Purification by column chromatography (silica eluted with petroleum ether/ethyl acetate 9:1) gave 5-t-butyl-2-thiophenecarboxaldehyde (21.01 g, 87%) as a yellow liquid.

Workup

  1. customa yellow solid was produced
  2. extractionextracted into diethyl ether
  3. washThe ethereal extracts were washed with water
  4. dry with materialdried over anhydrous sodium sulphate
  5. customthe solvent removed
  6. customto give a brown liquid
  7. customPurification
  8. washby column chromatography (silica eluted with petroleum ether/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-fdeb923407a547fab46ba3675c7ac867
Source dataset
uspto-grants-1988_05
Patent number
US04743602

Reaction notes

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