Tributylphosphine → HCID 58629833, compound

HRID 1391756Notes

Reaction equation

HRID 1391756 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.O[C:24]1[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:26][CH:25]=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:24]3[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:26][CH:25]=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 2736435Ethyl 4-hydroxyhydrocinnamateHCID 586298221-{6-[4-(Trifluoromethyl)phenyl]-2-pyridinyl}-1-pentanol

Product 1

HCID 58629833HCID 58629833, compoundYield 37.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of the 1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}-1-pentanol (50 mg, 0.16 mmol) and ethyl 3-(4-hydroxyphenyl)propanoate (31 mg, 0.16 mmol) in anhydrous THF (3.2 mL) under nitrogen at 0° C. (ice/water bath) was added ADDM (83 mg, 0.32 mmol). After a few minutes, nBu3P (81 μL, 0.32 mmol) was added (drop-wise) and the solution was stirred at 0° C. warming to rt overnight. After 17.5 hours the solvent was concentrated under vacuum and the solid residue dissolved in DCM (5 mL) and washed with water (5 mL) using a hydrophobic frit. The aqueous layer was re-extracted with DCM (5 mL) and the combined organic layers concentrated under vacuum. The resulting solid residue was then purified by SPE (silica, 5 g cartridge) eluting with cyclohexane:EtOAc (gradient 100:1 to 1:1) to afford the title compound (29 mg).

Workup

  1. waitAfter a few minutes
  2. temperaturewarming to rt overnight
  3. concentrationAfter 17.5 hours the solvent was concentrated under vacuum
  4. dissolutionthe solid residue dissolved in DCM (5 mL)
  5. washwashed with water (5 mL)
  6. extractionThe aqueous layer was re-extracted with DCM (5 mL)
  7. concentrationthe combined organic layers concentrated under vacuum
  8. customThe resulting solid residue was then purified by SPE (silica, 5 g cartridge)
  9. washeluting with cyclohexane

Sources & evidence

ORD record
ord-2e293668acca4d868a0d8b360e3613a5
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

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