Toluene → HCID 69358489, compound

HRID 860679Notes

Reaction equation

HRID 860679 reaction equation
[CH:1]([C:4]1[N:5]=[C:6]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)[O:7][C:8]=1[CH:9]([CH3:12])[CH2:10][OH:11])([CH3:3])[CH3:2].[CH3:23][O:24][C:25](=[O:35])[CH2:26][C:27]1[CH:32]=[CH:31][C:30](O)=[CH:29][C:28]=1[CH3:34].C1(C)C=CC=CC=1.C(P(CCCC)CCCC)CCC>CCOCC>[CH3:23][O:24][C:25](=[O:35])[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([O:11][CH2:10][CH:9]([C:8]2[O:7][C:6]([C:13]3[CH:14]=[CH:15][C:16]([C:19]([F:21])([F:22])[F:20])=[CH:17][CH:18]=3)=[N:5][C:4]=2[CH:1]([CH3:2])[CH3:3])[CH3:12])=[CH:29][C:28]=1[CH3:34]

Participants

6

Reactant 4

HCID 1140TolueneHCID 13831TributylphosphineHCID 57431971HCID 57431971, compoundHCID 58765710HCID 58765710, compound

Product 1

HCID 69358489HCID 69358489, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2-[4-Isopropyl-2-(4-trifluoromethyl-phenyl)-oxazol-5-yl]-propan-1-ol, (0.18 g, 0.5745 mmol), (4-Hydroxy-2-methyl-phenyl)-acetic acid methyl ester (0.114 g) and toluene (10 mL) and azodicarboxylic dipiperidide (0.19 g, 0.747 mmol) is stirred at −20 deg C. Neat tri-n-butyl phosphine (0.19 mL, 0.747 mmol) is added dropwise and the resulting mixture is allowed to reach room temperature with stirring 18 hr. The mixture is diluted with ether (25 mL) and cooled in ice/water for 30 min. The mixture is filtered, concentrated, and purified via silica gel chromatography eluting with 95:5 hexanes:ethyl acetate to afford the title compound as a thick oil, 0.065 g, 24%. MS M++1 476. The structure is confirmed by 1H NMR spectroscopy.

Workup

  1. customto reach room temperature
  2. stirringwith stirring 18 hr
  3. filtrationThe mixture is filtered
  4. concentrationconcentrated
  5. custompurified via silica gel chromatography
  6. washeluting with 95:5 hexanes

Sources & evidence

ORD record
ord-73b1a05c7c304a13b2cadd3cfc4a1472
Source dataset
uspto-grants-2006_12
Patent number
US07153878B2

Reaction notes

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