Hydrochloric Acid → HCID 58071508, compound

HRID 1256025Notes

Reaction equation

HRID 1256025 reaction equation
[CH:1]([P:3](=[O:17])([CH:15]=[CH2:16])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[C:6]([O:13][CH3:14])[CH:5]=1)=[CH2:2].[C:18]([O:26][CH2:27][CH3:28])(=[O:25])[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21].C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O>[CH3:14][O:13][C:6]1[CH:5]=[C:4]([P:3]2(=[O:17])[CH2:15][CH2:16][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])([C:18]([O:26][CH2:27][CH3:28])=[O:25])[CH2:2][CH2:1]2)[CH:9]=[CH:8][C:7]=1[N+:10]([O-:12])=[O:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7761Diethyl MalonateHCID 11430Potassium CarbonateHCID 58071501HCID 58071501, compound2×

Product 1

HCID 58071508HCID 58071508, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
75 °C

Procedure

Diethenyl(3-methoxy-4-nitrophenyl)phosphane oxide (INTERMEDIATE 58) (0.45 g, 1.78 mmol) and diethyl malonate (0.285 g, 1.78 mmol) were added to a 15 mL round-bottomed flask. DMSO (10 mL) was added to give a brown solution. Potassium carbonate (0.368 g, 2.67 mmol) was added. The reaction was heated to 75° C. and stirred at that temp for 1 h. The reaction was cooled to RT, and the solution was poured into an HCl solution (1N, 40 mL). The mixture was extracted with EtOAc (3×10 mL), and the combined organic layers were dried (Na2SO4) and concentrated to give the crude product. The crude product was added to a silica gel column (40 g) and eluted with MeOH/DCM (0-5%). The collected fractions were concentrated to give the product (0.3 g, 41%).

Workup

  1. customto give a brown solution
  2. temperatureThe reaction was cooled to RT
  3. extractionThe mixture was extracted with EtOAc (3×10 mL)
  4. dry with materialthe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated
  6. customto give the crude product
  7. washeluted with MeOH/DCM (0-5%)
  8. concentrationThe collected fractions were concentrated

Sources & evidence

ORD record
ord-31fd0fbafd7f4aaa95acd7bc5da5bcd5
Source dataset
uspto-grants-2013_06
Patent number
US08461170B2

Reaction notes

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