Monobenzone → 1-(4-Fluorophenyl)-3-(4-benzyloxyphenoxy)methyl-2-methyl-5-(4-methylsulfonylphenyl)pyrrole

HRID 1937356Notes

Reaction equation

HRID 1937356 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=3)=[CH:11][C:10]([CH2:23][OH:24])=[C:9]2[CH3:25])=[CH:4][CH:3]=1.CCOC(/N=N/C(OCC)=O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:57]([O:64][C:65]1[CH:70]=[CH:69][C:68](O)=[CH:67][CH:66]=1)[C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1>C1COCC1.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:20])=[O:21])=[CH:15][CH:14]=3)=[CH:11][C:10]([CH2:23][O:24][C:68]3[CH:69]=[CH:70][C:65]([O:64][CH2:57][C:58]4[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=4)=[CH:66][CH:67]=3)=[C:9]2[CH3:25])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 7638MonobenzoneHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 105463821-(4-Fluorophenyl)-4-hydroxymethyl-5-methyl-2-(4-methylsulfonylphenyl)pyrrole

Product 1

HCID 224606781-(4-Fluorophenyl)-3-(4-benzyloxyphenoxy)methyl-2-methyl-5-(4-methylsulfonylphenyl)pyrrole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Compound 6 (from Example A) (1 mmol) is added to a solution of diethylazodicarboxylate (1 mmol) and triphenylphosphine (1 mmol) in dry THF (10 mL). 4-Benzyloxyphenol (7) (1 mmol) is then added, and the progress of the reaction is monitored by tlc. When the reaction is complete, water is added and the product is extracted with ethyl acetate. The extract is dried and evaporated and the title compound 8 is then purified by HPLC.

Workup

  1. extractionthe product is extracted with ethyl acetate
  2. customThe extract is dried
  3. customevaporated
  4. customthe title compound 8 is then purified by HPLC

Sources & evidence

ORD record
ord-3ced224f996f4aeea09e49630ca88572
Source dataset
uspto-grants-2002_05
Patent number
US06395724B1

Reaction notes

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