HCID 14877941, compound → HCID 14877942, compound

HRID 1608396Notes

Reaction equation

HRID 1608396 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)=[C:9]([N:12]2[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:15][N:14]=[N:13]2)[CH2:10][OH:11])=[CH:4][CH:3]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:23]2[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=2)=[C:9]([N:12]2[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:15][N:14]=[N:13]2)[CH:10]=[O:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14877941HCID 14877941, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 14877942HCID 14877942, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3.2 g (8.2 mmoles) of 3,3-bis(4-fluorophenyl)-2-(5-phenyl-1H-tetrazol-1-yl)-2-propenol in 200 mL of dry methylene chloride at room temperature was added 1.9 g (8.8 mmoles) of pulverized pyridinium chlorochromate in a single portion. The oxidation was allowed to proceed at room temperature for 24 hours. The crude reaction suspension was diluted with 200 mL of hexanes and the resulting dark brownish suspension was filtered through a bed (1 cm thick) of fine silica gel. The pale filtrate was collected and evaporated under reduced pressure to give the desired product. The solid was recrystallized from an ethyl acetate-hexanes mixture to yield 2.9 g (91.1%) of the title compound; m.p.=193.0°-194.5° C.

Workup

  1. customThe crude reaction suspension
  2. filtrationthe resulting dark brownish suspension was filtered through a bed (1 cm thick) of fine silica gel
  3. customThe pale filtrate was collected
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-427276e69d534d5cb619d108403d4ef4
Source dataset
uspto-grants-1989_09
Patent number
US04870187

Reaction notes

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