Nitroethane → HCID 59168906, compound

HRID 2178142Notes

Reaction equation

HRID 2178142 reaction equation
[F:1][C:2]([F:6])([F:5])[CH:3]=[CH2:4].[N+:7]([CH2:10][CH3:11])([O-])=[O:8].C1(N=C=O)C=CC=CC=1>C(OCC)C>[CH3:11][C:10]1[CH2:4][CH:3]([C:2]([F:6])([F:5])[F:1])[O:8][N:7]=1

Participants

5

Reactant 3

HCID 6587NitroethaneHCID 7672Phenyl isocyanateHCID 126723,3,3-Trifluoropropene

Product 1

HCID 59168906HCID 59168906, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
22 °C

Procedure

To a solution of 3,3,3-trifluoroprop-1-ene (ca. 18 g) in diethyl ether (120 ml) was added subsequently at −78° C. nitroethane (5.74 g, 76.5 mmol), TEA (76 mg, 0.75 mmol) and phenyl isocyanate (18.2 g, 153 mmol), the solution was warmed to 22° C. and stirring was continued for 60 h. The suspension was filtered and the filtrate distilled from bulb to bulb at 75° C./1.0 mbar to give 3-methyl-5-(trifluoromethyl)-4,5-dihydroisoxazole (4.69 g) as a pale yellow liquid. MS: m/z=153 [M]+.

Workup

  1. filtrationThe suspension was filtered
  2. distillationthe filtrate distilled from bulb to bulb at 75° C./1.0 mbar

Sources & evidence

ORD record
ord-e8c0bfaea8174a64bb2aafc2fca95ccb
Source dataset
uspto-grants-2015_06
Patent number
US09067926B2

Reaction notes

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