3,3-Bis(4-fluorophenyl)-2-[1-(1-methylethyl)-1H-tetrazol-5-yl]-2-propenol → 3,3-Bis(4-fluorophenyl)-2-[1-(1-methylethyl)-1H-tetrazol-5-yl]-2-propenal

HRID 330638Notes

Reaction equation

HRID 330638 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)=[C:9]([C:12]2[N:16]([CH:17]([CH3:19])[CH3:18])[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:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)=[C:9]([C:12]2[N:16]([CH:17]([CH3:19])[CH3:18])[N:15]=[N:14][N:13]=2)[CH:10]=[O:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 147238723,3-Bis(4-fluorophenyl)-2-[1-(1-methylethyl)-1H-tetrazol-5-yl]-2-propenolHCID 178418287HCID 178418287, compound

Product 1

HCID 147238733,3-Bis(4-fluorophenyl)-2-[1-(1-methylethyl)-1H-tetrazol-5-yl]-2-propenalYield 53.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The allylic alcohol (0.96 g) prepared in Step C was dissolved in 45 mL of dry methylene chloride at room temperature and to this vigorousy stirred solution was added 0.64 g (2.96 mmoles) pyridinium chlorchromate in one single portion. After the reaction mixture was stirred for four hours an analytical TLC eluted once with 10% EtOAc in hexanes (v/v) and twice with 20% EtOAc in hexanes (v/v) showed one major product spot at Rf =0.22. The crude mixture was poured onto a bed of silica gel about 1/2 inches thick and eluted with 20% EtOAc in hexanes to give 0.51 g (53%) of the title compound. MS (CI): m/e=355 for (M+H)+.

Workup

  1. stirringAfter the reaction mixture was stirred for four hours an analytical TLC
  2. washeluted once with 10% EtOAc in hexanes (v/v) and twice with 20% EtOAc in hexanes (v/v)
  3. additionThe crude mixture was poured onto a bed of silica gel about 1/2 inches thick
  4. washeluted with 20% EtOAc in hexanes

Sources & evidence

ORD record
ord-3eb2bbd1b7814f38806b041c701b9fe1
Source dataset
uspto-grants-1990_01
Patent number
US04897490

Reaction notes

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