Hydrochloric Acid → HCID 68771470, compound

HRID 2098564Notes

Reaction equation

HRID 2098564 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[CH:12]([C:14]1[CH:19]=[CH:18][C:17](/[CH:20]=[CH:21]/[C:22]([O:24][CH3:25])=[O:23])=[CH:16][CH:15]=1)=O.C(OC(=O)C)(=O)C.C(N(C(C)C)CC)(C)C.Cl>C(OCC)(=O)C.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[CH:12][C:14]2[CH:15]=[CH:16][C:17](/[CH:20]=[CH:21]/[C:22]([O:24][CH3:25])=[O:23])=[CH:18][CH:19]=2)[C:9]([OH:11])=[O:10])=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 98372-(4-Fluorophenyl)acetic acidHCID 81531DiisopropylethylamineHCID 11008713methyl (2E)-3-(4-formylphenyl)prop-2-enoate

Product 1

HCID 68771470HCID 68771470, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
30 °C

Procedure

A mixture of 4-fluorophenylacetic acid (2.5 g, 13.2 mmol) and methyl (E)-3-(4-formylphenyl)acrylate (2.03 g, 13.2 mmol) were dissolved under stirring with acetic anhydride (8 mL). To this mixture, diisopropylethylamine (DIPEA) (3.4 mL, 19.7 mmol) was added and stirred at 30° C. for 2 hours. Upon completion (as monitored by TLC using 100% ethyl acetate as eluent), the reaction mixture was poured into water and the pH adjusted to 1 using dilute HCl (1:1). The aqueous layer was extracted with ethyl acetate (2×150 mL). The combined ethyl acetate layer was washed with water till the washings were neutral and dried over anhydrous Na2SO4. The ethyl acetate layer was evaporated to dryness to obtain a sticky compound and further triturated with cold dichloromethane (DCM) to furnish a white solid. The solid obtained was filtered and dried under vacuum to afford the title compound (2 g, 47% yield).

Workup

  1. dissolutionwere dissolved
  2. extractionThe aqueous layer was extracted with ethyl acetate (2×150 mL)
  3. washThe combined ethyl acetate layer was washed with water till the washings
  4. dry with materialdried over anhydrous Na2SO4
  5. customThe ethyl acetate layer was evaporated to dryness
  6. customto obtain a sticky compound
  7. customfurther triturated with cold dichloromethane (DCM)
  8. customto furnish a white solid
  9. customThe solid obtained
  10. filtrationwas filtered
  11. customdried under vacuum

Sources & evidence

ORD record
ord-c520d875a2bf412f845d78e1d3c55cc0
Source dataset
uspto-grants-2013_05
Patent number
US08450525B2

Reaction notes

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