Sodium Acetate → HCID 20069270, compound

HRID 982156Notes

Reaction equation

HRID 982156 reaction equation
[CH2:1]([Sn:5]([CH2:24][CH2:25][CH2:26][CH3:27])([CH2:20][CH2:21][CH2:22][CH3:23])[C:6]1[CH:7]=[C:8]([NH:12][C:13](=[O:19])/[CH:14]=[CH:15]\[C:16](O)=[O:17])[CH:9]=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH3:4].C([O-])(=O)C.[Na+]>C(OC(=O)C)(=O)C>[CH2:1]([Sn:5]([CH2:20][CH2:21][CH2:22][CH3:23])([CH2:24][CH2:25][CH2:26][CH3:27])[C:6]1[CH:7]=[C:8]([N:12]2[C:16](=[O:17])[CH:15]=[CH:14][C:13]2=[O:19])[CH:9]=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 67938515135861-52-8

Product 1

HCID 20069270HCID 20069270, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

N-(m tri-n butylstannylphenyl)maleamic acid prepared as described above (0.40 g, 0.83 mmol) was placed in acetic anhydride (6 mL). Sodium acetate (0.43 g) was added and the solution stirred for 15 minutes at room temperature. After the reaction became homogeneous, the reaction mixture was stirred for 3 hours at 120° C. The filtrate obtained from this brown mixture was evaporated to dryness under reduced pressure and the residue was dissolved in ethyl ether. The ether mixture was filtered and the filtrate was again evaporated to dryness The compound was obtained by flash chromatography on a 30×200 mm column of Kieselgel 60, 230-400 mesh, eluted with ethyl acetate/hexane (1:5) (100 mL) to yield ten fractions. Fractions 6-9 were combined to give the desired product as an orange oil (0.3, 78%): TLC (EtOAc/hexane, 1:5) Rf 0.30; 1H NMR (CDCl3), δ); 7.3-7.5 (multiplets, 4H, 4 aryl CH); 6.8 (singlet, 2H, 2 CHC=O); 0.9-1.6 (multiplets, 27H, 3×n-C4H9).

Workup

  1. stirringthe reaction mixture was stirred for 3 hours at 120° C
  2. customThe filtrate obtained from this brown mixture
  3. customwas evaporated to dryness under reduced pressure
  4. dissolutionthe residue was dissolved in ethyl ether
  5. filtrationThe ether mixture was filtered
  6. customthe filtrate was again evaporated to dryness The compound
  7. customwas obtained by flash chromatography on a 30×200 mm column of Kieselgel 60, 230-400 mesh
  8. washeluted with ethyl acetate/hexane (1:5) (100 mL)
  9. customto yield ten fractions

Sources & evidence

ORD record
ord-a6cc4f6e102849b59953a36435580069
Source dataset
uspto-grants-1991_02
Patent number
US04994557

Reaction notes

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