Tributylphosphine → HCID 69207846, compound

HRID 1391740Notes

Reaction equation

HRID 1391740 reaction equation
P(CCCC)(CCCC)CCCC.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[F:28][C:29]([F:49])([F:48])[C:30]1[CH:35]=[CH:34][C:33]([C:36]2[N:41]=[C:40]([CH:42]([OH:47])[CH2:43][CH2:44][CH2:45][CH3:46])[CH:39]=[CH:38][CH:37]=2)=[CH:32][CH:31]=1.O[C:51]1[CH:65]=[CH:64][C:54]([O:55][C:56]([CH3:63])([CH3:62])[C:57]([O:59][CH2:60][CH3:61])=[O:58])=[C:53]([CH3:66])[CH:52]=1>C1COCC1>[CH3:63][C:56]([O:55][C:54]1[CH:64]=[CH:65][C:51]([O:47][CH:42]([C:40]2[CH:39]=[CH:38][CH:37]=[C:36]([C:33]3[CH:32]=[CH:31][C:30]([C:29]([F:48])([F:28])[F:49])=[CH:35][CH:34]=3)[N:41]=2)[CH2:43][CH2:44][CH2:45][CH3:46])=[CH:52][C:53]=1[CH3:66])([CH3:62])[C:57]([O:59][CH2:60][CH3:61])=[O:58]

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 16756990Ethyl 2-(4-hydroxy-2-methylphenoxy)-2-methylpropanoateHCID 586298221-{6-[4-(Trifluoromethyl)phenyl]-2-pyridinyl}-1-pentanol

Product 1

HCID 69207846HCID 69207846, compoundYield 10.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of nBu3P (47 μL, 0.19 mmol) in dry THF (2 mL), at 0° C. (ice/water bath) under nitrogen was added DIAD (37 mL, 0.19 mmol). After stirring for 10 minutes 1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}-1-pentanol (50 mg, 0.16 mmol) was added, followed after another 20 minutes by ethyl 2-(4-hydroxy-2-methylphenoxy)-2-methylpropanoate (39 mg, 0.16 mmol). The mixture was then allowed to warm to rt over 16 hours and was then reduced under vacuum and the residue partitioned between EtOAc and water. The layers were separated and the organic layer washed with water (2×) then brine, dried (Na2SO4) and reduced to give a brown gum. Purification by Biotage™ chromatography (silica, 40 g cartridge) eluting with cyclohexane:EtOAc (19:1) afforded the title compound as a colourless gum (9 mg).

Workup

  1. additionwas added
  2. customthe residue partitioned between EtOAc and water
  3. customThe layers were separated
  4. washthe organic layer washed with water (2×)
  5. dry with materialbrine, dried (Na2SO4)
  6. customto give a brown gum
  7. customPurification by Biotage™ chromatography (silica, 40 g cartridge)
  8. washeluting with cyclohexane:EtOAc (19:1)

Sources & evidence

ORD record
ord-23401cb86c904c4cbf031ede89911cf4
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

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