Tetrahydrofuran → HCID 44435656, compound

HRID 916021Notes

Reaction equation

HRID 916021 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:27][CH3:28])=[C:6]([C:8]([CH3:26])([CH3:25])[CH2:9][C:10]([OH:24])([C:20]([F:23])([F:22])[F:21])[CH2:11][C:12]2[CH:19]=[CH:18][C:15]([C:16]#N)=[CH:14][CH:13]=2)[CH:7]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C1C[O:38]CC1>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:27][CH3:28])=[C:6]([C:8]([CH3:26])([CH3:25])[CH2:9][C:10]([OH:24])([C:20]([F:23])([F:22])[F:21])[CH2:11][C:12]2[CH:19]=[CH:18][C:15]([CH:16]=[O:38])=[CH:14][CH:13]=2)[CH:7]=1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 10287444HCID 10287444, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 44435656HCID 44435656, compoundYield 18%

Procedure

To a solution of 79 mg (0.2 mmol) of 4-[4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]benzonitrile in 10 mL of THF was added 11.3 mg (0.3 mmol) of lithium aluminum hydride and the mixture was warmed to reflux. After 18 hours, all the solvent escaped. The reaction was cooled to room temperature, THF was added, and the reaction was quenched with water and extracted with EtOAc. The combined organic extracts were dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by preparative TLC (silica gel, toluene-EtOAc (95:5)) to leave an oil. A second purification by preparative TLC (silica gel, hexanes-EtOAc (9:1)) afforded 15 mg (18%) of the title compound as an oil which partially solidified.

Workup

  1. temperaturethe mixture was warmed to reflux
  2. customthe reaction was quenched with water
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by preparative TLC (silica gel, toluene-EtOAc (95:5))
  8. customto leave an oil
  9. customA second purification by preparative TLC (silica gel, hexanes-EtOAc (9:1))

Sources & evidence

ORD record
ord-ed70e098eb1345d19dddfeef2e2c7137
Source dataset
uspto-grants-2007_09
Patent number
US07268152B2

Reaction notes

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