Dimethylformamide → HCID 45094683, compound

HRID 907115Notes

Reaction equation

HRID 907115 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[CH:5]=[CH:4]1)[CH3:2].O=P(Cl)(Cl)Cl.CN([CH:22]=[O:23])C>>[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5]([CH:22]=[O:23])=[CH:4]1)[CH3:2]

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 59425473HCID 59425473, compound

Product 1

HCID 45094683HCID 45094683, compoundYield 81%

Procedure

1-Ethyl-6-methoxy-1H-indole (900 mg, 5.14 mmol) was dissolved in DMF (1.5 mL). This was added dropwise to an ice-cold solution of POCl3 (500 μL, 5.2 mmol) in DMF (1.75 ml). After stirring at room temperature for 90 minutes, the reaction mixture was re-cooled in an ice bath and was slowly quenched with 6N NaOH (4 mL). The reaction mixture was partitioned between EtOAc and H2O. Purification by silica gel chromatography (EtOAc/CH2Cl2, 5/95) yielded 1-ethyl-6-methoxy-1H-indole-3-carbaldehyde (849 mg, 81%) as a yellow solid.

Workup

  1. temperaturethe reaction mixture was re-cooled in an ice bath
  2. customwas slowly quenched with 6N NaOH (4 mL)
  3. customThe reaction mixture was partitioned between EtOAc and H2O
  4. customPurification by silica gel chromatography (EtOAc/CH2Cl2, 5/95)

Sources & evidence

ORD record
ord-a4dccf501be64e96afb0262c061895b9
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

Loading…