Tributylphosphine → HCID 58629891, compound

HRID 1391784Notes

Reaction equation

HRID 1391784 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[C:29]([CH3:30])=[CH:28][C:27](/[CH:31]=[CH:32]/[C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:26][C:25]=1[CH3:38].C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1.CCCCP(CCCC)CCCC>C1COCC1>[CH3:38][C:25]1[CH:26]=[C:27](/[CH:31]=[CH:32]/[C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH:28]=[C:29]([CH3:30])[C:24]=1[O:20][CH:15]([C:13]1[CH:12]=[CH:11][CH:10]=[C:9]([C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:21])([F:1])[F:22])=[CH:8][CH:7]=2)[N:14]=1)[CH2:16][CH2:17][CH2:18][CH3:19]

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 19361036HCID 19361036, compoundHCID 586298221-{6-[4-(Trifluoromethyl)phenyl]-2-pyridinyl}-1-pentanol

Product 1

HCID 58629891HCID 58629891, compoundYield 34.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}-1-pentanol (62 mg, 0.20 mmol) and ethyl (2E)-3-(4-hydroxy-3,5-dimethylphenyl)-2-propenoate (79 mg, 0.36 mmol) in THF (4 mL) at 0° C. under nitrogen was added ADDP (101 mg, 0.40 mmol) followed by tri-N-butylphosphine (0.100 mL, 0.40 mmol). The resulting mixture was then allowed to warm slowly to ambient temperature overnight. After 66 h the solvent was removed under vacuum (Genevac) and the resulting solid partitioned between DCM (5 mL) and water (5 mL), the layers separated and the aqueous re-extracted with DCM (5 mL). The combined organic layer was then reduced under vacuum and purified by SPE (silica, 10 g cartridge) eluting with cyclohexane:EtOAc (gradient 20:1 to 1:1) to give the title compound (35 mg).

Workup

  1. customAfter 66 h the solvent was removed under vacuum (Genevac)
  2. customthe resulting solid partitioned between DCM (5 mL) and water (5 mL)
  3. customthe layers separated
  4. extractionthe aqueous re-extracted with DCM (5 mL)
  5. custompurified by SPE (silica, 10 g cartridge)
  6. washeluting with cyclohexane

Sources & evidence

ORD record
ord-1938df07b3d3446c92b428ddfd36ba34
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

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