Tributylphosphine → HCID 58629943, compound

HRID 1391752Notes

Reaction equation

HRID 1391752 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[C:13]([CH:15]([OH:20])[CH2:16][CH2:17][CH2:18][CH3:19])[CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[CH3:23][O:24][C:25](=[O:34])[CH2:26][C:27]1[CH:32]=[CH:31][C:30](O)=[CH:29][CH:28]=1.P(CCCC)(CCCC)CCCC>C1COCC1>[F:22][C:2]([F:21])([F:1])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:14]=[C:13]([CH:15]([O:20][C:30]3[CH:31]=[CH:32][C:27]([CH2:26][C:25]([O:24][CH3:23])=[O:34])=[CH:28][CH:29]=3)[CH2:16][CH2:17][CH2:18][CH3:19])[CH:12]=[CH:11][CH:10]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 13831TributylphosphineHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl esterHCID 586298221-{6-[4-(Trifluoromethyl)phenyl]-2-pyridinyl}-1-pentanol

Product 1

HCID 58629943HCID 58629943, compoundYield 63.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}-1-pentanol (349 mg, 1.13 mmol) in dry THF (22.5 mL) at 0° C. (ice/water bath) under nitrogen was added methyl-4-hydroxyphenylacetate (187 mg, 1.13 mmol) followed after 1 minute by ADDM (578 mg, 2.25 mmol) in one portion. The resulting orange cloudy mixture was stirred for 3 minutes and then treated with nBu3P (562 μL, 2.26 mmol) drop-wise over 1 minute. The resulting pale yellow/orange mixture was then allowed to warm slowly to rt over 64 hours. The cloudy mixture was then reduced under vacuum and the residue partitioned between EtOAc (50 mL) and water (50 mL) and the layers separated. The aqueous was then re-extracted with EtOAc (50 mL) and the combined organic layer washed with brine (100 mL) dried (MgSO4), filtered and reduced to give an oil which was purified by SPE (silica) eluting with cyclohexane:EtOAc (gradient 100:1 to 5:1) to give the title compound (330 mg).

Workup

  1. customthe residue partitioned between EtOAc (50 mL) and water (50 mL)
  2. customthe layers separated
  3. extractionThe aqueous was then re-extracted with EtOAc (50 mL)
  4. washthe combined organic layer washed with brine (100 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customto give an oil which
  8. customwas purified by SPE (silica)
  9. washeluting with cyclohexane

Sources & evidence

ORD record
ord-47457907db634f87aa44eb5c49bb0093
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

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