Ethylene Glycol → trans 2,3-dihydro-6-fluoro-2-(2-phenylethyl)-4H-1-benzopyran-4-carboxylic acid

HRID 2248294Notes

Reaction equation

HRID 2248294 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH:9]([CH2:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:8]C(C#N)[C:6]=2[CH:21]=1.[OH-:22].[K+].[CH2:24]([OH:27])[CH2:25]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:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:8][C@H:25]([C:24]([OH:27])=[O:22])[C:6]=2[CH:21]=1

Participants

4

Reactant 3

HCID 174Ethylene GlycolHCID 14797Potassium HydroxideHCID 190944432,3-dihydro-6-fluoro-4-cyano-2-(2-phenylethyl)-4H-1-benzopyran

Product 1

HCID 53827237trans 2,3-dihydro-6-fluoro-2-(2-phenylethyl)-4H-1-benzopyran-4-carboxylic acid

Procedure

2,3-dihydro-6-fluoro-4-cyano-2-(2-phenylethyl)-4H-1-benzopyran (2.7 gm) and solid KOH (2.7 gm) were suspended in ethylene glycol (100 mL) and heated under reflux for 1.5 hours, then poured onto ice/H2O (300 mL), and extracted with diethyl ether, and the organic extracts discarded. The aqueous layer was acidified to pH 1 with 6N HCl, and extracted with ethyl acetate, and the extracts washed with H2O, brine, dried, filtered and evaporated to yield the title compound (2.9 gm, m.p. 105°-108° C.).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1.5 hours
  3. additionpoured onto ice/H2O (300 mL)
  4. extractionextracted with diethyl ether
  5. extractionextracted with ethyl acetate
  6. washthe extracts washed with H2O, brine
  7. customdried
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-c190c1dce8ab422f9bc03f36a722e246
Source dataset
uspto-grants-1991_08
Patent number
US05039672

Reaction notes

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