Tributylphosphine → (6-{2-[5-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-ethoxy}-benzofuran-3-yl)-acetic acid methyl ester

HRID 490770Notes

Reaction equation

HRID 490770 reaction equation
[CH3:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:17][CH2:18][OH:19].C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1.C(P(CCCC)CCCC)CCC.[CH3:51][O:52][C:53](=[O:65])[CH2:54][C:55]1[C:59]2[CH:60]=[CH:61][C:62](O)=[CH:63][C:58]=2[O:57][CH:56]=1>C1(C)C=CC=CC=1.O>[CH3:51][O:52][C:53](=[O:65])[CH2:54][C:55]1[C:59]2[CH:60]=[CH:61][C:62]([O:19][CH2:18][CH2:17][C:3]3[N:4]=[C:5]([C:7]4[CH:8]=[CH:9][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:11][CH:12]=4)[S:6][C:2]=3[CH3:1])=[CH:63][C:58]=2[O:57][CH:56]=1

Participants

7

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 20770861Methyl 2-(6-hydroxy-1-benzofuran-3-yl)acetateHCID 226474902-[5-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-ethanol

Product 1

HCID 57675482(6-{2-[5-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-ethoxy}-benzofuran-3-yl)-acetic acid methyl esterYield 33%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

To a solution of 2-[5-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-ethanol (0.12 g, 0.43 mmol) in toluene (3 mL) at 0° C. is added ADDP (0.14 g, 0.57 mmol) followed by tri-n-butylphosphine (0.14 mL, 0.56 mmol). A toluene solution of (6-Hydroxy-benzofuran-3-yl)-acetic acid methyl ester (0.52 g, 1.22 mmol) is added, and the mixture is allowed to warm to RT overnight. Water is added, and the aqueous phase is extracted with EtOAc. The organics are dried with MgSO4 and purified by flash chromatography to yield the title compound (0.066 g, 33%).

Workup

  1. extractionthe aqueous phase is extracted with EtOAc
  2. dry with materialThe organics are dried with MgSO4
  3. custompurified by flash chromatography

Sources & evidence

ORD record
ord-1e39dc89aa9343e1bbf5e362de2afa7f
Source dataset
uspto-grants-2009_05
Patent number
US07528160B2

Reaction notes

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