Tributylphosphine → HCID 86604658, compound

HRID 1391755Notes

Reaction equation

HRID 1391755 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[CH:36]=[CH:35][C:27]([O:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:26][CH:25]=1.P(CCCC)(CCCC)CCCC>C1COCC1>[F:22][C:2]([F:21])([F:1])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:14]=[C:13]([CH:15]([O:20][C:26]3[CH:25]=[CH:24][CH:36]=[CH:35][C:27]=3[O:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:16][CH2:17][CH2:18][CH3:19])[CH:12]=[CH:11][CH:10]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 13831TributylphosphineHCID 13187337Ethyl 2-(4-hydroxyphenoxy)acetateHCID 586298221-{6-[4-(Trifluoromethyl)phenyl]-2-pyridinyl}-1-pentanol

Product 1

HCID 86604658HCID 86604658, compoundYield 26.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}-1-pentanol (99 mg, 0.32 mmol) in dry THF (6.4 mL) at 0° C. (ice/water bath) under nitrogen was added ethyl (4-hydroxyphenoxy)acetate (63 mg, 0.32 mmol) followed after 1 minute by ADDM (164 mg, 0.64 mmol) in one portion. The resulting orange slurry was stirred for 2 minutes and then treated with nBu3P (159 μL, 0.64 mmol) drop-wise over 1 minute. The resulting pale yellow/orange mixture was then allowed to warm slowly to rt over 69 hours. The cloudy mixture was then reduced under vacuum and the residue purified by SPE (silica) eluting with cyclohexane:EtOAc (gradient 100:1 to 1:1) to give the title compound (42 mg).

Workup

  1. customthe residue purified by SPE (silica)
  2. washeluting with cyclohexane

Sources & evidence

ORD record
ord-063273da89334390bbcb62dcd202b5f6
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

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