Tributylphosphine → 5-(Tert-butyldiphenylsilyloxymethyl)-4-[[4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenoxy]methyl]-2-phenyl-1,3-oxazole

HRID 2221801Notes

Reaction equation

HRID 2221801 reaction equation
[Si:1]([O:18][CH2:19][C:20]1[O:24][C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[N:22][C:21]=1[CH2:31][OH:32])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(P(CCCC)CCCC)CCC.[CH3:46][C:47]1[O:51][C:50]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)=[N:49][C:48]=1[CH2:58][O:59][C:60]1[CH:65]=[CH:64][C:63](O)=[CH:62][CH:61]=1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1>[Si:1]([O:18][CH2:19][C:20]1[O:24][C:23]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[N:22][C:21]=1[CH2:31][O:32][C:63]1[CH:62]=[CH:61][C:60]([O:59][CH2:58][C:48]2[N:49]=[C:50]([C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)[O:51][C:47]=2[CH3:46])=[CH:65][CH:64]=1)([C:14]([CH3:15])([CH3:16])[CH3:17])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 11189974[5-(Tert-butyldiphenylsilyloxymethyl)-2-phenyl-1,3-oxazol-4-yl]methanolHCID 68884209HCID 68884209, compound

Product 1

HCID 692168795-(Tert-butyldiphenylsilyloxymethyl)-4-[[4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenoxy]methyl]-2-phenyl-1,3-oxazoleYield 81.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of [5-(tert-butyldiphenylsilyloxymethyl)-2-phenyl-1,3-oxazol-4-yl]methanol (1.11 g), tributylphosphine (1.01 g), 4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenol (0.70 g) and tetrahydrofuran (80 mL) was added 1,1′-(azodicarbonyl)dipiperidine (1.26 g) at room temperature, and the mixture was stirred for 15 hrs. The precipitated crystals were removed by filtration and the filtrate was concentrated. The residue was subjected to silica gel column chromatography to give 5-(tert-butyldiphenylsilyloxymethyl)-4-[[4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenoxy]methyl]-2-phenyl-1,3-oxazole as an oil (1.44 g, yield 81%) from a fraction eluted with ethyl acetate-hexane (1:4, v/v).

Workup

  1. customThe precipitated crystals were removed by filtration
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-a265c9a6385d46c7bc9756ab4e80dc19
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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