Dimethylformamide → HCID 86758571, compound

HRID 991787Notes

Reaction equation

HRID 991787 reaction equation
[CH:1]1[NH:5][CH:4]=[C:3]2[C:6](=[O:10])[O:7][CH2:8][CH2:9][C:2]=12.CN(C)[CH:13]=[O:14].P(Cl)(Cl)(Cl)=O>ClCCl>[O:10]=[C:6]1[C:3]2[CH2:2][CH2:1][N:5]([CH:13]=[O:14])[C:4]=2[CH2:9][CH2:8][O:7]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 22135434HCID 22135434, compound

Product 1

HCID 86758571HCID 86758571, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6,7-Dihydro-2H-pyrano[3,4-c]pyrrol-4-one (5 g, 36 mmol) was formulated under standard Vilsmeier reaction using N,N-dimethylformamide (DMF, 1.2 eq.) and phosphorus oxychloride (POCl3, 1.1 eq.) in dichloromethane. The above mixture was stirred at room temperature for 1 hour. The precipitate salt was filtered, washed with dichloromethane, suspended in water and made basic with 6 N sodium hydroxide to pH=12. The mixture was stirred for 5 minutes and filtered. The solid was washed with ethanol/water mixture (1:1) to give 3.5 g (58%) of 4-oxo-2,4,6,7-tetrahydro-pyrano[3,4]pyrrole-1-carbaldehyde.

Workup

  1. filtrationThe precipitate salt was filtered
  2. washwashed with dichloromethane
  3. stirringThe mixture was stirred for 5 minutes
  4. filtrationfiltered
  5. washThe solid was washed with ethanol/water mixture (1:1)

Sources & evidence

ORD record
ord-25b3ee74deb04c3fb44d1b071f6249ba
Source dataset
uspto-grants-2002_10
Patent number
US06465507B2

Reaction notes

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