Tributylphosphine → Ethyl ({2-methyl-4-[(1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}hexyl)oxy]phenyl}oxy)acetate

HRID 1391760Notes

Reaction equation

HRID 1391760 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[C:13]([CH:15]([OH:21])[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.O[C:25]1[CH:37]=[CH:36][C:28]([O:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[C:27]([CH3:38])[CH:26]=1.P(CCCC)(CCCC)CCCC>C1COCC1>[CH3:38][C:27]1[CH:26]=[C:25]([O:21][CH:15]([C:13]2[CH:12]=[CH:11][CH:10]=[C:9]([C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:22])([F:1])[F:23])=[CH:8][CH:7]=3)[N:14]=2)[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH:37]=[CH:36][C:28]=1[O:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32]

Participants

5

Reactant 3

HCID 13831TributylphosphineHCID 21986458Ethyl (4-hydroxy-2-methylphenoxy)acetateHCID 586298791-{6-[4-(Trifluoromethyl)phenyl]-2-pyridinyl}-1-hexanol

Product 1

HCID 58629912Ethyl ({2-methyl-4-[(1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}hexyl)oxy]phenyl}oxy)acetateYield 37.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}-1-hexanol (131 mg, 0.41 mmol) in dry THF (15 mL) under nitrogen was cooled to 0° C. and treated with ethyl (4-hydroxy-2-methylphenoxy)acetate (85 mg, 0.41 mmol), ADDM (210 mg, 0.82 mmol) and nBu3P (204 μL, 0.82 mmol). The reaction mixture was then allowed to warm to rt slowly over 22 hours. The solvent was removed under vacuum and the residue partitioned between EtOAc (2×30 mL) and water (30 mL). The layers were separated and the organic layer dried (Na2SO4) and reduced. Purification by SPE (silica, 20 g cartridge) eluting with cyclohexane:EtOAc (49:1 to 24:1) afforded the title compound as a colourless oil (80 mg).

Workup

  1. customThe solvent was removed under vacuum
  2. customthe residue partitioned between EtOAc (2×30 mL) and water (30 mL)
  3. customThe layers were separated
  4. dry with materialthe organic layer dried (Na2SO4)
  5. customPurification by SPE (silica, 20 g cartridge)
  6. washeluting with cyclohexane:EtOAc (49:1 to 24:1)

Sources & evidence

ORD record
ord-c4c81f9a902e4678aea1c511d5a34af5
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

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