Tributylphosphine → Ethyl [(4-{[1-(6-bromo-2-pyridinyl)pentyl]oxy}-2-ethylphenyl)oxy]acetate

HRID 1391764Notes

Reaction equation

HRID 1391764 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH:8]([OH:13])[CH2:9][CH2:10][CH2:11][CH3:12])[CH:5]=[CH:4][CH:3]=1.O[C:15]1[CH:27]=[CH:26][C:18]([O:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:17]([CH2:28][CH3:29])[CH:16]=1.C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1.P(CCCC)(CCCC)CCCC>C1COCC1>[Br:1][C:2]1[N:7]=[C:6]([CH:8]([O:13][C:15]2[CH:27]=[CH:26][C:18]([O:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:17]([CH2:28][CH3:29])[CH:16]=2)[CH2:9][CH2:10][CH2:11][CH3:12])[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 58580457(2-Ethyl-4-hydroxyphenoxy)acetic Acid Ethyl EsterHCID 586299071-(6-Bromo-2-pyridinyl)-1-pentanol

Product 1

HCID 58629868Ethyl [(4-{[1-(6-bromo-2-pyridinyl)pentyl]oxy}-2-ethylphenyl)oxy]acetateYield 66.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1-(6-bromo-2-pyridinyl)-1-pentanol (250 mg, 1.02 mmol) and ethyl (4-hydroxy-2-ethylphenoxy)acetate (230 mg, 1.02 mmol) in dry THF (21 mL) at 0° C. (ice/water bath) under nitrogen was added ADDP (517 mg, 2.04 mmol) followed by nBu3P (510 μL, 2.04 mmol) drop-wise. The mixture was stirred with slow warming to rt over 18 hours and then concentrated under vacuum, diluted with EtOAc (150 mL) and washed with water (3×75 mL), dried (MgSO4), filtered and reduced to give an oil. Purification by SPE (silica, 10 g Cartridge) eluting with cyclohexane:EtOAc (gradient 20:1 to 5:1) afforded the title compound (307 mg).

Workup

  1. concentrationconcentrated under vacuum
  2. additiondiluted with EtOAc (150 mL)
  3. washwashed with water (3×75 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customto give an oil
  7. customPurification by SPE (silica, 10 g Cartridge)
  8. washeluting with cyclohexane

Sources & evidence

ORD record
ord-164528ad53234411b69ec08ef113db97
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

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