Potassium Hydroxide → HCID 13883256, compound

HRID 1608264Notes

Reaction equation

HRID 1608264 reaction equation
[OH-].[K+].[F:3][C:4]1[CH:25]=[CH:24][C:7]([CH2:8][C:9]2[CH2:13][C:12]([CH2:19][O:20]C(=O)C)([CH2:14][O:15]C(=O)C)[O:11][N:10]=2)=[CH:6][CH:5]=1>C(O)C>[F:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][C:9]2[CH2:13][C:12]([CH2:19][OH:20])([CH2:14][OH:15])[O:11][N:10]=2)=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 13883255HCID 13883255, compound

Product 1

HCID 13883256HCID 13883256, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 58.3 g of KOH in 900 ml of ethanol is added to 138 g of 3-(p-fluorobenzyl)-5,5-bis-(acetoxymethyl)-isoxazoline, and the mixture is refluxed for 12 hours. After the mixture has been cooled, the precipitated salt is filtered off and the solvent is removed under reduced pressure. Acetone is added, after which precipitated solid is again filtered off under suction and the filtrate is evaporated down. The oil obtained can be purified by column chromatography [silica gel; eluent: toluene/acetone (initially 9/1, subsequently 1/1)]. 83 g of 3-(p-fluorobenzyl)-5,5-bis-(hydroxymethyl)-isoxazoline of melting point 93°-97° C. are obtained. ##STR12##

Workup

  1. temperaturethe mixture is refluxed for 12 hours
  2. temperatureAfter the mixture has been cooled
  3. filtrationthe precipitated salt is filtered off
  4. customthe solvent is removed under reduced pressure
  5. additionAcetone is added
  6. customafter which precipitated solid
  7. filtrationis again filtered off under suction
  8. customthe filtrate is evaporated down
  9. customThe oil obtained can
  10. custombe purified by column chromatography [silica gel

Sources & evidence

ORD record
ord-4e561411ad9c41f6b514f5ed9917a1e1
Source dataset
uspto-grants-1989_09
Patent number
US04870100

Reaction notes

Loading…