Dimethylformamide → 2,3-Dihydrobenzofuran-5-carboxaldehyde

HRID 661594Notes

Reaction equation

HRID 661594 reaction equation
P(Cl)(Cl)(Cl)=O.[O:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][CH2:7]1.CN([CH:18]=[O:19])C>>[O:6]1[C:10]2[CH:11]=[CH:12][C:13]([CH:18]=[O:19])=[CH:14][C:9]=2[CH2:8][CH2:7]1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 10329DihydrobenzofuranHCID 24813Phosphorus oxychloride

Product 1

HCID 7359012,3-Dihydrobenzofuran-5-carboxaldehydeYield 85%

Conditions

Temperature
82.5 °C

Procedure

Phosphorous oxychloride (255.58 g, 1.666 mol) was slowly added to a solution of DMF (355.0 ml) and 2,3-dihydrobenzofuran (100 g, 0.833 mol) maintaining the temperature 80-85° C. The reaction mixture was stirred for 4-5 hr and the reaction progress monitored by HPLC. The reaction mixture was then poured into ice water and extracted with toluene (2000 ml). The organic layer was washed with 5% sodium bicarbonate solution (500 ml) and then 10% brine solution (500 ml). The organic layer was distilled off under vacuum at 50-60° C. A liquid product was isolated. Yield: 85-90%, Purity: 90-92%

Workup

  1. extractionextracted with toluene (2000 ml)
  2. washThe organic layer was washed with 5% sodium bicarbonate solution (500 ml)
  3. distillationThe organic layer was distilled off under vacuum at 50-60° C
  4. customA liquid product was isolated

Sources & evidence

ORD record
ord-cfc6c3296bc64eac93964d1b15d6c655
Source dataset
uspto-grants-2011_12
Patent number
US08084630B2

Reaction notes

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