Dimethylformamide → HCID 25140192, compound

HRID 661350Notes

Reaction equation

HRID 661350 reaction equation
CN([CH:4]=[O:5])C.P(Br)(Br)[Br:7].[O:10]1[CH2:15][CH2:14][C:13](=O)[CH2:12][CH2:11]1.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[Br:7][C:13]1[CH2:14][CH2:15][O:10][CH2:11][C:12]=1[CH:4]=[O:5]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24614Phosphorus tribromideHCID 121599Tetrahydro-4H-pyran-4-oneHCID 516892Sodium Bicarbonate

Product 1

HCID 25140192HCID 25140192, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
25 °C

Procedure

A mixture of DMF (10 mL) and chloroform (200 mL) at 5° C. was treated with PBr3 (10 mL), stirred at 25° C. for 40 minutes, treated with tetrahydropyran-4-one (5 g) in chloroform (50 mL) at 0° C., stirred at 25° C. for 18 hours, poured onto ice, treated with sodium bicarbonate, and extracted with diethyl ether. The extract was washed with saturated sodium bicarbonate and brine and dried (MgSO4), filtered and concentrated. The concentrate was flash chromatographed on silica gel with 10% ethyl acetate/hexanes.

Workup

  1. stirringstirred at 25° C. for 18 hours
  2. additionpoured onto ice
  3. extractionextracted with diethyl ether
  4. washThe extract was washed with saturated sodium bicarbonate and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customchromatographed on silica gel with 10% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-84d1688f296d44e297dab359809155f7
Source dataset
uspto-grants-2011_12
Patent number
US08084607B2

Reaction notes

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