Tributylphosphine → HCID 58765676, compound

HRID 860672Notes

Reaction equation

HRID 860672 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH:16]([CH3:19])[CH2:17][OH:18])=[C:11]([CH:13]([CH3:15])[CH3:14])[N:12]=2)=[CH:4][CH:3]=1.[CH3:20][O:21][C:22](=[O:33])[CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28](O)=[CH:27][C:26]=1[CH3:32].C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1(C)C=CC=CC=1>[CH3:20][O:21][C:22](=[O:33])[CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:18][CH2:17][CH:16]([C:10]2[O:9][C:8]([C:5]3[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=3)=[N:12][C:11]=2[CH:13]([CH3:15])[CH3:14])[CH3:19])=[CH:27][C:26]=1[CH3:32]

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 13551833Methyl 3-(4-Hydroxy-2-methylphenyl)propanoateHCID 58765780HCID 58765780, compound

Product 1

HCID 58765676HCID 58765676, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2-[2-(4-bromo-phenyl)-4-isopropyl-oxazol-5-yl]-propan-1-ol (225 mg, 0.694 mmol) and 3-(4-hydroxy-2-methyl-phenyl)-propionic acid methyl ester (190 mg, 0.972 mmol) in toluene (15 mL) is degassed and filled with nitrogen for 3 times. Tributylphosphine (224 mg, 1.11 mmol) is added to the reaction mixture under nitrogen at 0° C., followed by addition of of 1,1′-(azodicarbonyl)-dipiperidine (280 mg, 1.11 mmol). The reaction mixture is allowed to warm to room temperature and stirred overnight, the mixture is loaded directly on silica gel column chromatography with 10–15% EtOAc/Hexanes to afford the title compound (320 mg, 92%).

Workup

  1. additionfilled with nitrogen for 3 times

Sources & evidence

ORD record
ord-014ede4196a74a34872c723d29b4bbd9
Source dataset
uspto-grants-2006_12
Patent number
US07153878B2

Reaction notes

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