Dimethylformamide → 7-(benzyloxy)-4-methyl-2H-chromene-3-carbaldehyde

HRID 217431Notes

Reaction equation

HRID 217431 reaction equation
CN([CH:4]=[O:5])C.O=P(Cl)(Cl)Cl.[CH2:11]([O:18][C:19]1[CH:28]=[C:27]2[C:22]([C:23]([CH3:29])=[CH:24][CH2:25][O:26]2)=[CH:21][CH:20]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(Cl)Cl>[CH2:11]([O:18][C:19]1[CH:28]=[C:27]2[C:22]([C:23]([CH3:29])=[C:24]([CH:4]=[O:5])[CH2:25][O:26]2)=[CH:21][CH:20]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 584387087-(Benzyloxy)-4-methyl-2H-chromene

Product 1

HCID 584387777-(benzyloxy)-4-methyl-2H-chromene-3-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To DMF (1 mL) was added dropwise POCl3 (0.25 mL) at 0° C., followed by stirring at room temperature for 30 minutes. To the reaction mixture was added dropwise a solution of 7-(benzyloxy)-4-methyl 2H-chromene (280 mg) in DCM (1 mL), followed by stirring at room temperature for 3 hours. The reaction liquid was poured into ice-water, followed by extraction with EtOAc three times. The organic layer was combined, washed with water and brine in this order, dried over MgSO4, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (automatic purification device, hexane:EtOAc=85:15 to 70:30) to obtain 7-(benzyloxy)-4-methyl-2H-chromene-3-carbaldehyde (234 mg) as a pale yellow powder.

Workup

  1. stirringby stirring at room temperature for 3 hours
  2. customThe reaction liquid
  3. extractionfollowed by extraction with EtOAc three times
  4. washwashed with water and brine in this order
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (automatic purification device, hexane:EtOAc=85:15 to 70:30)

Sources & evidence

ORD record
ord-863e120b5ca64b4c8a0d27a8523b316e
Source dataset
uspto-grants-2012_06
Patent number
US08193378B2

Reaction notes

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