Tributylphosphine → HCID 58629821, compound

HRID 1391749Notes

Reaction equation

HRID 1391749 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]([OH:19])[CH2:15][CH2:16][CH2:17][CH3:18])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.P(CCCC)(CCCC)CCCC.O[C:34]1[CH:46]=[CH:45][C:37]([O:38][CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41])=[C:36]([CH3:47])[CH:35]=1.C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]([O:19][C:34]3[CH:46]=[CH:45][C:37]([O:38][CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41])=[C:36]([CH3:47])[CH:35]=3)[CH2:15][CH2:16][CH2:17][CH3:18])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 21986458Ethyl (4-hydroxy-2-methylphenoxy)acetateHCID 22760362HCID 22760362, compound

Product 1

HCID 58629821HCID 58629821, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(4′-chloro-4-biphenylyl)-1-pentanol (140 mg, 0.51 mmol) in dry THF (15 mL) under nitrogen at 0° C. (ice/water bath) was added nBu3P (250 μL, 1.02 mmol), followed by ethyl (4-hydroxy-2-methylphenoxy)acetate (110 mg, 0.52 mmol) and ADDP (260 mg, 1.03 mmol) portion-wise. After stirring the mixture for 18 hours at rt under nitrogen the solvent was removed under vacuum. The residue was partitioned between water and EtOAc and extracted with EtOAc (3×30 mL). The organic extract was separated and dried (MgSO4) and the solvent removed under vacuum. Purification by flash chromatography (silica) eluting with cyclohexane:EtOAc (9:1) afforded the title compound as a colourless gum (150 mg).

Workup

  1. customwas removed under vacuum
  2. customThe residue was partitioned between water and EtOAc
  3. extractionextracted with EtOAc (3×30 mL)
  4. extractionThe organic extract
  5. customwas separated
  6. dry with materialdried (MgSO4)
  7. customthe solvent removed under vacuum
  8. customPurification by flash chromatography (silica)
  9. washeluting with cyclohexane:EtOAc (9:1)

Sources & evidence

ORD record
ord-9936debe0c394460bc3be1b99d9ec59f
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

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