Dichloromethane → HCID 131716808, compound

HRID 358981Notes

Reaction equation

HRID 358981 reaction equation
C([C:3]1(CC)[C:7](=[O:8])[O:6][N:5]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH2:10])[C:4]1=[O:17])C.C(Cl)Cl.CCCCCC.O1C(=O)CC(=O)N1>C(Cl)(Cl)Cl.CCCCCC>[C:11]1([C:9]([N:5]2[C:4](=[O:17])[CH2:3][C:7](=[O:8])[O:6]2)=[CH2:10])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8058HexaneHCID 14851197HCID 14851197, compoundHCID 219431841,2-Oxazolidine-3,5-dione

Product 1

HCID 131716808HCID 131716808, compound

Reagents, catalysts & solvents 1

HCID 21585165Chloroform hexaneSolvent2×

Procedure

Analysis of crude 4,4-diethyl-2-(1phenylethenyl) isoxazolidine 3,5-dione was performed by thin layer chromatography (TLC) on Bakerflex Silica Plates using methylene chloride:-hexane (98:2) as the mobile phase. Components appeared at Rf 0.80, 0.78, 0.72, 0.60, 0.52, and 0.0. A sample of the crude isoxazolidine-3,5-dione weighing 3.50 g (38.4% purity by HPLC) was dissolved in 5.0 ml of chloroform:hexane (98:2), and applied to a 37×2 cm (O. D.) chromatography column containing 60-200 mesh silica gel as the adsorbant. The eluting solvent was chloroform:hexane (98:2) and the elution rate was 1 ml/min. Twenty 50 ml fractions were collected and analyzed by TLC as described above Fractions 11, 12, 13 and 14 showed a single component, Rf 0.60. These fractions were combined and concentrated to give 1.0 g of pure 4,4-diethyl-2-(1-phenylethenyl-isoxazolidine-3,5-dione as a viscous oil: IR(neat) 2976(w), 2938(w), 2882(w), 1816(s), 1721(s) and 1626 (s)cm-1 ; UV max (CH3OH) 245 nm (ε6800); 1H NMR (CDCl3) δ 7.72 (s, overlapping a small m, 5, aromatic CH) 5.47 (s, 1, vinyl CH), 5.34 (s, 1, vinyl CH), 1.83 (q, 4, CH2) and 0.91 (t, 6, CH3); high resolution MS, calc'd for: C15H17NO3 : 259.1208. Found: 259.1209; MS m/z (rel. intensity) 259 (44), 215 (48), 199 (85), 108 (89) and 106 (100). Elemental Analysis: Calc'd for: C15H17NO3 :C, 69.48; H, 6.61; N, 5.40.Found: C,69,64; H, 6.91; N, 5.04

Workup

  1. addition) chromatography column containing 60-200 mesh silica gel as the adsorbant
  2. customTwenty 50 ml fractions were collected
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-baf8d3f4bc7e42409eb760a0af255808
Source dataset
uspto-grants-1991_03
Patent number
US04999366

Reaction notes

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