Triethyl 2-phosphonopropionate → Ethyl 2-methyl-3-(3,4,5-trifluorophenyl)acrylate

HRID 1280867Notes

Reaction equation

HRID 1280867 reaction equation
[CH3:1][CH2:2][O:3][C:4]([CH:6](P(OCC)(OCC)=O)[CH3:7])=[O:5].C([Li])CCC.[F:21][C:22]1[CH:23]=[C:24]([CH:27]=[C:28]([F:31])[C:29]=1[F:30])[CH:25]=O>C1COCC1.CCCCCC.O.C([O-])([O-])=O.[Na+].[Na+]>[CH3:7][C:6](=[CH:25][C:24]1[CH:23]=[C:22]([F:21])[C:29]([F:30])=[C:28]([F:31])[CH:27]=1)[C:4]([O:3][CH2:2][CH3:1])=[O:5]

Participants

8

Reactant 3

HCID 107155Triethyl 2-phosphonopropionateHCID 27769543,4,5-TrifluorobenzaldehydeHCID 178418339Butyllithium

Product 1

HCID 53919072Ethyl 2-methyl-3-(3,4,5-trifluorophenyl)acrylate

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolventHCID 10340Sodium CarbonateSolvent

Procedure

4.3 ml of triethyl 2-phosphonopropionate are dissolved in 30 ml of anhydrous THF and 12.5 ml of a 1.6 N solution of n-butyllithium in hexane are added dropwise at 0° C. The mixture is stirred at RT for 15 minutes and a solution of 3.2 g of 3,4,5-trifluorobenzaldehyde in 8 ml of anhydrous THF is then added dropwise. It is stirred at RT for one hour and allowed to stand at RT for 16 hours. The reaction mixture is diluted with 300 ml of water, 30 ml of a saturated aqueous Na2CO3 solution are added and it is extracted 3 times using 100 ml of EA each time. The extract is dried over Na2SO4 and the solvent is removed in vacuo. Chromatography on silica gel using EA/HEP 1:8 yields 3.8 g if colorless crystals; m.p. 54° C.

Workup

  1. stirringIt is stirred at RT for one hour
  2. waitto stand at RT for 16 hours
  3. additionare added
  4. extractionit is extracted 3 times
  5. dry with materialThe extract is dried over Na2SO4
  6. customthe solvent is removed in vacuo
  7. customyields 3.8 g if colorless crystals

Sources & evidence

ORD record
ord-be83a979b3554b44acc1227633c531c1
Source dataset
uspto-grants-2002_09
Patent number
US06451781B1

Reaction notes

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