3,3,3-Trifluoropropene → HCID 71662965, compound

HRID 2178139Notes

Reaction equation

HRID 2178139 reaction equation
[F:1][C:2]([F:6])([F:5])[CH:3]=[CH2:4].C(=O)(O)[O-].[Na+].Cl/[C:13](=[N:19]\[OH:20])/[C:14]([O:16][CH2:17][CH3:18])=[O:15]>CCOC(C)=O>[F:1][C:2]([F:6])([F:5])[CH:3]1[O:20][N:19]=[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:4]1

Participants

5

Reactant 3

HCID 126723,3,3-TrifluoropropeneHCID 516892Sodium BicarbonateHCID 95760052-Chloro-2-hydroxyiminoacetic acid ethyl ester

Product 1

HCID 71662965HCID 71662965, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
22 °C

Procedure

To a suspension of 3,3,3-trifluoroprop-1-ene (ca. 4.3 g, 45 mmol) in AcOEt (30 ml) and sodium bicarbonate (6.3 g, 75.0 mmol) was added at −78° C. a solution of (Z)-ethyl 2-chloro-2-(hydroxyimino)acetate (2.81 g, 18.0 mmol) in AcOEt (6 ml), the suspension was allowed to warm to 22° C. and stirring was continued for 60 h. The suspension was filtered, the filtrate was evaporated and the residue purified by chromatography on silica gel using heptane/AcOEt (10:1) to give ethyl 5-(trifluoromethyl)-4,5-dihydroisoxazole-3-carboxylate (3.2 g) as a colorless oil. MS: m/z=211 [M]+.

Workup

  1. filtrationThe suspension was filtered
  2. customthe filtrate was evaporated
  3. customthe residue purified by chromatography on silica gel

Sources & evidence

ORD record
ord-1aab34cb236147a5bb97097e889d078a
Source dataset
uspto-grants-2015_06
Patent number
US09067926B2

Reaction notes

Loading…