Triphenylphosphine → 2-(2-{3-[2-(4-Benzyloxyphenyl)-5-methyl-1H-pyrrol-1-yl]propoxy}phenyl)-1,3-benzoxazole

HRID 1072762Notes

Reaction equation

HRID 1072762 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:16]([CH2:21][CH2:22][CH2:23][OH:24])[C:17]([CH3:20])=[CH:18][CH:19]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[C:32]1[O:33][C:34]2[CH:40]=[CH:39][CH:38]=[CH:37][C:35]=2[N:36]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1(C)C=CC=CC=1.O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:16]([CH2:21][CH2:22][CH2:23][O:24][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]3[O:33][C:34]4[CH:40]=[CH:39][CH:38]=[CH:37][C:35]=4[N:36]=3)[C:17]([CH3:20])=[CH:18][CH:19]=2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 132692-(2-Benzoxazolyl)phenolHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 223873173-[2-(4-Benzyloxyphenyl)-5-methyl-1H-pyrrol-1-yl]propan-1-ol

Product 1

HCID 223874662-(2-{3-[2-(4-Benzyloxyphenyl)-5-methyl-1H-pyrrol-1-yl]propoxy}phenyl)-1,3-benzoxazoleYield 59.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-[2-(4-benzyloxyphenyl)-5-methyl-1H-pyrrol-1-yl]propan-1-ol (1.00 g, 3.11 mmol), 2-(2-hydroxyphenyl)benzoxazole (986 mg, 4.67 mmol) and triphenylphosphine (1.22 g, 4.67 mmol) in toluene (2 ml) was added 1,1′-(azodicarbonyl)dipiperidine (1.18 g, 4.67 mmol) and the mixture was stirred at 80° C. for 12 hours. The reaction solution was poured into water and the mixture was extracted with ethyl acetate. The extract was dried over magnesium sulfate anhydride and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:1) to give the object compound as an oily substance. 950 mg (yield: 59.4%)

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over magnesium sulfate anhydride
  3. customthe solvent was removed under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:1)
  5. customto give the object compound as an oily substance

Sources & evidence

ORD record
ord-169a0c9ad21c44739e5b54008a5136b0
Source dataset
uspto-grants-2005_06
Patent number
US06911468B2

Reaction notes

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