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

HRID 330637Notes

Reaction equation

HRID 330637 reaction equation
[Cl-].[F:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)=[C:10]([C:13]2[N:17]([CH:18]([CH3:20])[CH3:19])[N:16]=[N:15][N:14]=2)[CH2:11][OH:12])=[CH:5][CH:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].OS(O)(=O)=O>O1CCCC1>[F:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)=[C:10]([C:13]2[N:17]([CH:18]([CH3:20])[CH3:19])[N:16]=[N:15][N:14]=2)[CH2:11][OH:12])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 199862413,3-Bis(4-fluorophenyl)-2-[1-(1-methylethyl)-1H-tetrazol-5-yl]-2-propenolchlorideHCID 21226445Aluminium lithium hydride

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The acid chloride prepared in Step B was dissolved in 20 ml of dry tetrahydrofuran followed by the slow addition of 1.8 mL of lithium aluminum hydride (1.0 Molar in tetrahydrofran) under an argon atmosphere at -78° C. Analytical TLC eluted once with 30% EtOAc in hexanes (v/v) showed the alcohol product at Rf =0.46. The crude reaction mixture was poured into dilute H2SO4 (2N in H2O) and the desired product was extracted with three portions (40 mL×3)) of diethyl ether. The organic extracts were combined, dried over MgSO4 and concentrated under reduced pressure to give 1.07 g of the title compound which was used without further purification in the next step.

Workup

  1. washAnalytical TLC eluted once with 30% EtOAc in hexanes (v/v)
  2. customThe crude reaction mixture
  3. extractionthe desired product was extracted with three portions (40 mL×3)) of diethyl ether
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f1d22540198d4e74b474c6ea1505feae
Source dataset
uspto-grants-1990_01
Patent number
US04897490

Reaction notes

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