Dimethylformamide → 5-tert-Butylfuran-2-carbaldehyde

HRID 1252468

Reaction equation

HRID 1252468 reaction equation
P(Cl)(Cl)(Cl)=O.CN(C)[CH:8]=[O:9].[C:11]([C:15]1[O:16][CH:17]=[CH:18][CH:19]=1)([CH3:14])([CH3:13])[CH3:12].C(=O)([O-])[O-].[Na+].[Na+]>>[C:11]([C:15]1[O:16][C:17]([CH:8]=[O:9])=[CH:18][CH:19]=1)([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 1389032-tert-Butylfuran

Product 1

HCID 136961955-tert-Butylfuran-2-carbaldehydeYield 99%

Conditions

Temperature
10 °C

Procedure

Phosphorus oxychloride (26.75 g, 0.174 mol) was added dropwise to dimethylformamide (12.92 g, 0.177 mol). This mixture was cooled to 10° C. for 1/2 hour, then 2-t-butylfuran (18.45 g, 0.149 mol) was added dropwise and the mixture stirred at room temperature for 3 hours. The mixture was poured into ice/water, neutralised with sodium carbonate 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 oil. Purification by column chromatography (silica eluted with petroleum ether/ethyl acetate 9:1) gave 5-t-butyl-2-furancarboxaldehyde (22.46 g, 99%).

Workup

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

Sources & evidence

ORD record
ord-8fe82d54f6334289974b91c862db7191
Source dataset
uspto-grants-1988_05
Patent number
US04743602

Linked notes

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