Tetrahydrofuran → HCID 23324898, compound

HRID 1380917Notes

Reaction equation

HRID 1380917 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:25])([C:16](=[O:24])[C:17]([F:23])([F:22])[C:18]([F:21])([F:20])[F:19])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1.[CH3:26][Mg]Br.O1CCCC1.[Cl-].[NH4+]>[Na].CCOCC.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:25])([C:16]([CH3:26])([OH:24])[C:17]([F:22])([F:23])[C:18]([F:19])([F:21])[F:20])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 23324897HCID 23324897, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 23324898HCID 23324898, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolventHCID 5360545SodiumSolvent

Procedure

2-(2,4-Difluorophenyl)-2-hydroxy-4,4,5,5,5-pentafluoro-1-(1H-1,2,4-triazol-1-yl)pentan-3-one (0.5 g; 0.00135 moles) was dissolved in sodium-dried diethyl ether (50 cm3) and methylmagnesium bromide (1.35 cm3 of a 3M solution in ether; 0.00405 moles) was added. Dry tetrahydrofuran (15 cm3) was then added. The mixture was heated at reflux for 2 hours, cooled and 5% aqueous ammonium chloride (50 cm3) was added, followed by ethyl acetate (100 cm3). The phases were separated and the organic phase was dried (MgSO4) and evaporated. The residue was purified by flash column chromatography on 230-400 mesh silica, eluting with ethyl acetate:diethylamine (95:5, 500 cm3). Two diastereomers were recovered by collection and evaporation of appropriate fractions. The first diastereomer to be eluted was called diastereomer I.

Workup

  1. addition0.00405 moles) was added
  2. temperatureThe mixture was heated
  3. temperatureat reflux for 2 hours
  4. temperaturecooled
  5. customThe phases were separated
  6. dry with materialthe organic phase was dried (MgSO4)
  7. customevaporated
  8. customThe residue was purified by flash column chromatography on 230-400 mesh silica
  9. washeluting with ethyl acetate:diethylamine (95:5, 500 cm3)
  10. customTwo diastereomers were recovered by collection and evaporation of appropriate fractions
  11. washThe first diastereomer to be eluted

Sources & evidence

ORD record
ord-1a4bc0f788c746ce8407ed0c66a59216
Source dataset
uspto-grants-1986_04
Patent number
US04584307

Reaction notes

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