18-Crown-6 → HCID 15190126, compound

HRID 1033733Notes

Reaction equation

HRID 1033733 reaction equation
C([O-])(=[O:3])C.[K+].[F:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[C:14]1([C:17]([S:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)([CH3:19])[CH3:18])[CH2:16][O:15]1.C1OCCOCCOCCOCCOCCOC1>O.CC(N(C)C)=O>[F:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[C:14]([OH:3])([C:17]([S:20][CH2:21][C:22]1[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=1)([CH3:19])[CH3:18])[CH2:16][OH:15]

Participants

6

Reactant 3

HCID 2855718-Crown-6HCID 517044Potassium AcetateHCID 19024387HCID 19024387, compound

Product 1

HCID 15190126HCID 15190126, compoundYield 75.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 31374DimethylacetamideSolvent

Conditions

Temperature
110 °C

Procedure

A solution of 1.12 g (11.4 mmol) of potassium acetate in 2 ml of water was added to a solution of 2.0 g (5.7 mmol) of (±)-2-(2,4-difluorophenyl)-2-(1-((4-methoxyphenyl)methylthio)-1-methylethyl)oxirane and 0.15 g (0.57 mmol) of 18-crown-6 in 12 ml of DMA, and the mixture was stirred at 110° C. for 30 hours. After being allowed to cool, 50 ml of water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution, dried, and distilled under reduced pressure to remove the solvent. The residue was purified by column chromatography using a mixed solvent of hexane and ethyl acetate (5:1) as an eluent. The solvent was removed by distillation under reduced pressure, and the residue was recrystallized from a mixed solvent of isopropyl ether and diethyl ether to obtain 1.58 g (75%) of (±)-2-(2,4-difluorophenyl)-3-((4-methoxyphenyl)methylthio)- 3-methylbutane-1,2-diol as a colorless crystal.

Workup

  1. temperatureto cool
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  4. customdried
  5. distillationdistilled under reduced pressure
  6. customto remove the solvent
  7. customThe residue was purified by column chromatography
  8. customThe solvent was removed by distillation under reduced pressure
  9. customthe residue was recrystallized from a mixed solvent of isopropyl ether and diethyl ether

Sources & evidence

ORD record
ord-0c8c54887ece481eadac3a829666736e
Source dataset
uspto-grants-1994_05
Patent number
US05312815

Reaction notes

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