Nitroethane → HCID 54125846, compound

HRID 1417531Notes

Reaction equation

HRID 1417531 reaction equation
C(N(CC)CC)C.[Br:8][C:9]1[CH:14]=[C:13]([CH:15]=[CH:16][O:17][CH3:18])[CH:12]=[CH:11][C:10]=1[O:19][CH3:20].C1(N=C=O)C=CC=CC=1.[N+:30]([CH2:33][CH3:34])([O-])=[O:31]>C1(C)C=CC=CC=1.O>[Br:8][C:9]1[CH:14]=[C:13]([CH:15]2[CH:16]([O:17][CH3:18])[O:31][N:30]=[C:33]2[CH3:34])[CH:12]=[CH:11][C:10]=1[O:19][CH3:20]

Participants

7

Reactant 4

HCID 6587NitroethaneHCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 53925270HCID 53925270, compound

Product 1

HCID 54125846HCID 54125846, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Triethylamine (0.050 mL, 0.36 mmol) was added in portions to a mixture of 2-bromo-1-methoxy-4-(2-methoxyvinyl)benzene (500 mg, 2.06 mmol, 1:1 ratio of E- and Z-isomers), phenylisocyanate (0.489 mL, 4.5 mmol), and nitroethane (0.180 mL, 2.5 mmol) in dry toluene (2.0 mL) at room temperature. After stirring at room temperature for 5 h followed by 1 h at 100° C. for 1 h, the mixture was allowed to stand overnight at room temperature. Water (6 mL) was then added and stirring was continued at room temperature for 4 h. The mixture was filtered, the layers of the filtrate were separated, and the aqueous layer was extracted with 2×30 mL of toluene. The combined organic layers were dried over sodium sulfate and evaporated. Flash column chromatography on 50 g of silica gel eluting with 2 L of 10% of ethyl acetate/hexane yielded 4-(3-bromo-4-methoxyphenyl)-5-methoxy-3-methyl-4,5-dihydroisoxazole as 0.28 g of yellow oil containing some remaining impurity. 1H NMR (400 MHz, CDCl3): δ 7.33 (d, 1H, J=2 Hz), 7.03(dd, 1H, J=9, 2 Hz), 6.87 (d, 1H, J=9 Hz), 5.15 (d, 1H, J=1 Hz), 3.89 (s, 3H), 3.88 (s, 1H), 3.47 (s, 3H), 1.83 (s, 3H). Mass spectrum (NH3CI): m/e=300 (M+1).

Workup

  1. waitfollowed by 1 h at 100° C. for 1 h
  2. waitto stand overnight at room temperature
  3. stirringstirring
  4. waitwas continued at room temperature for 4 h
  5. filtrationThe mixture was filtered
  6. customthe layers of the filtrate were separated
  7. extractionthe aqueous layer was extracted with 2×30 mL of toluene
  8. dry with materialThe combined organic layers were dried over sodium sulfate
  9. customevaporated

Sources & evidence

ORD record
ord-287d0f708bea43929cda78b6fb5de389
Source dataset
uspto-grants-1999_03
Patent number
US05877191

Reaction notes

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