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

HRID 2248295ノート

反応式

HRID 2248295 の反応式
[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

参加物

4

反応物 3

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

生成物 1

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

反応条件

温度
0 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-b32f21125d3f42eeb6a8e11cb3db76db
出典データセット
uspto-grants-1991_08
特許番号
US05039672

反応ノート

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