Tributylphosphine → HCID 69589326, compound

HRID 860670Notes

Reaction equation

HRID 860670 reaction equation
[CH:1]([C:4]1[N:5]=[C:6]([C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]([F:22])([F:21])[F:20])=[CH:14][CH:13]=2)[O:7][C:8]=1[CH:9]([OH:11])[CH3:10])([CH3:3])[CH3:2].[CH3:23][O:24][C:25](=[O:36])[CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][C:31](O)=[CH:30][C:29]=1[CH3:35].C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1(C)C=CC=CC=1>[CH3:23][O:24][C:25](=[O:36])[CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][C:31]([O:11][CH:9]([C:8]2[O:7][C:6]([C:12]3[CH:17]=[CH:16][C:15]([O:18][C:19]([F:21])([F:22])[F:20])=[CH:14][CH:13]=3)=[N:5][C:4]=2[CH:1]([CH3:2])[CH3:3])[CH3:10])=[CH:30][C:29]=1[CH3:35]

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 13551833Methyl 3-(4-Hydroxy-2-methylphenyl)propanoateHCID 58765793HCID 58765793, compound

Product 1

HCID 69589326HCID 69589326, compoundYield 11.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1-[4-isopropyl-2-(4-trifluoromethoxy-phenyl)-oxazol-5-yl]-ethanol (140 mg, 0.446 mmol) and 3-(4-hydroxy-2-methyl-phenyl)-propionic acid methyl ester (122 mg, 0.624 mmol) in toluene (15 mL) is degassed and filled with nitrogen for 3 times. Tributylphosphine (144 mg, 0.713 mmol) is added to the reaction mixture under nitrogen at 0° C., followed by addition of of 1,1′-(azodicarbonyl)-dipiperidine (169 mg, 0.669 mmol). The reaction mixture is allowed to warm to room temperature and stirred for 4 hours. The mixture is loaded directly on silica gel column chromatography with 10–25% EtOAc/Hexanes to afford the title compound (25 mg, 11%).

Workup

  1. additionfilled with nitrogen for 3 times

Sources & evidence

ORD record
ord-5b0a903b1fcb4ab187765894a12c8796
Source dataset
uspto-grants-2006_12
Patent number
US07153878B2

Reaction notes

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