Water → HCID 69999794, compound

HRID 1633830Notes

Reaction equation

HRID 1633830 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:30])[CH:29]=1)[CH:25]=O.O>CCCCCC>[F:21][C:22]1[CH:23]=[C:24](/[CH:25]=[C:6](\[CH3:7])/[C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH:27]=[C:28]([F:30])[CH:29]=1

Participants

6

Reactant 4

HCID 962WaterHCID 107155Triethyl 2-phosphonopropionateHCID 5881603,5-DifluorobenzaldehydeHCID 178418339Butyllithium

Product 1

HCID 69999794HCID 69999794, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

5 a) 1 eq. of triethyl 2-phosphonopropionate was deprotonated at 0° C. with 1 eq. of n-butyllithium in hexane and then treated at RT with 1 eq. of 3,5-difluorobenzaldehyde. After the aldehyde had completely reacted, the mixture was worked up with water and extracted three times by shaking with toluene. After the combined organic phases had been dried over magnesium sulfate, the solvent was removed under vacuum and the residual crude product was separated by chromatography on silica gel using EE/HEP mixtures as the eluent. Ethyl E-3-(3,5-difluorophenyl)-2-methylacrylate was isolated.

Workup

  1. extractionextracted three times
  2. dry with materialAfter the combined organic phases had been dried over magnesium sulfate
  3. customthe solvent was removed under vacuum
  4. customthe residual crude product was separated by chromatography on silica gel using EE/HEP

Sources & evidence

ORD record
ord-81d47bc939dc4d799a622d2d70dcb72d
Source dataset
uspto-grants-2003_01
Patent number
US06504057B2

Reaction notes

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