Potassium Carbonate → (E)-1-[3-(4-Fluorophenoxy)phenyl]buten-3-one

HRID 704817Notes

Reaction equation

HRID 704817 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=2)[CH:10]=O)=[CH:4][CH:3]=1.[C:17]([CH2:20]P(=O)(OC)OC)(=[O:19])[CH3:18].C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[F:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:8]=[C:9](/[CH:10]=[CH:18]/[C:17](=[O:19])[CH3:20])[CH:12]=[CH:13][CH:14]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 77872Dimethyl (2-oxopropyl)phosphonateHCID 3085320Benzaldehyde, 3-(4-fluorophenoxy)-

Product 1

HCID 20073371(E)-1-[3-(4-Fluorophenoxy)phenyl]buten-3-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of the product from step (c) (8.9 g). dimethyl acetylmethylphosphonate (6.84 g), anhy. potassium carbonate (11.37 g) and dry THF (100 ml) was heated under N2 at 50°-55° C. for 20 hours. The mixture was then cooled and filtered, the residue washed with THF, and the filtrate and washings combined and stripped to give a pale orange oil which was eluted through a silica gel column using ether/40-60 pet. ether (1:2) and the eluate stripped and dried under high vacuum to give the desired product as a very pale yellow, viscous oil (5.59 g).

Workup

  1. temperatureThe mixture was then cooled
  2. filtrationfiltered
  3. washthe residue washed with THF
  4. customto give a pale orange oil which
  5. washwas eluted through a silica gel column
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-e17bb97c436d48ac8a9d00b639245b3e
Source dataset
uspto-grants-1991_01
Patent number
US04988733

Reaction notes

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