Hydrochloric Acid → trans methyl 2,3-dihydro-6-fluoro-2-(2-phenylethyl)-4H-1-benzopyran-4-carboxylate

HRID 2248295Notes

Reaction equation

HRID 2248295 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][C@@H:9]([CH2:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:8][C@H:7]([C:19]([OH:21])=[O:20])[C:6]=2[CH:22]=1.Cl.[CH3:24]O>>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][C@@H:9]([CH2:11][CH2:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:8][C@H:7]([C:19]([O:21][CH3:24])=[O:20])[C:6]=2[CH:22]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 53827237trans 2,3-dihydro-6-fluoro-2-(2-phenylethyl)-4H-1-benzopyran-4-carboxylic acid

Product 1

HCID 54538647trans methyl 2,3-dihydro-6-fluoro-2-(2-phenylethyl)-4H-1-benzopyran-4-carboxylate

Conditions

Temperature
0 °C

Procedure

Cis and trans 2,3-dihydro-6-fluoro-2-(2-phenylethyl)-4H-1-benzopyran-4-carboxylic acid (2.9 gm) was dissolved in methanol, cooled to 0° C., and the mixture saturated with gaseous HCl. After 24 hours, the mixture was concentrated in vacuo, and the residue partitioned between ethyl acetate and saturated sodium bicarbonate. The organic layer was washed with brine, dried (Na2SO4), filtered and evaporated. The residue was purified by column chromatography (2:1 hexane/diethyl ether, SiO2) to yield the title compound (1.9 gm, Rf=0.3,2:1 hexane/diethyl ether, SiO2).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customthe residue partitioned between ethyl acetate and saturated sodium bicarbonate
  3. washThe organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography (2:1 hexane/diethyl ether, SiO2)

Sources & evidence

ORD record
ord-b32f21125d3f42eeb6a8e11cb3db76db
Source dataset
uspto-grants-1991_08
Patent number
US05039672

Reaction notes

Loading…