1,1-dimethylethyl 4-[2-(1,1-dimethylethyl)-2H-tetrazol-5-yl]benzene propenoate → 5-[4-(3-(1,1-dimethylethoxy)-3-oxopropyl)phenyl]-2-(1,1-dimethylethyl)-2H-tetrazole

HRID 1721251Notes

Reaction equation

HRID 1721251 reaction equation
[C:1]([OH:5])(=[O:4])[CH:2]=[CH2:3].CC([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:17]=[N:18][N:19]([C:21]([CH3:24])([CH3:23])[CH3:22])[N:20]=2)=[CH:12][CH:11]=1)(C)C.[H][H]>C(O)C.[Pd]>[CH3:12][C:13]([CH3:16])([O:4][C:1](=[O:5])[CH2:2][CH2:3][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:17]=[N:18][N:19]([C:21]([CH3:23])([CH3:22])[CH3:24])[N:20]=2)=[CH:12][CH:11]=1)[CH3:14]

Participants

5

Reactant 2

HCID 867465281,1-dimethylethyl 4-[2-(1,1-dimethylethyl)-2H-tetrazol-5-yl]benzene propenoateHCID 178418361HCID 178418361, compound2×

Product 1

HCID 224172825-[4-(3-(1,1-dimethylethoxy)-3-oxopropyl)phenyl]-2-(1,1-dimethylethyl)-2H-tetrazoleYield 157.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 1,1-dimethylethyl 4-[2-(1,1-dimethylethyl)-2H-tetrazol-5-yl]benzene propenoate (1.6 g, 5.6 mmol) and 100 mg of 10% Pd/c in ethanol (17 mL) was stirred under a blanket of hydrogen (1 atm). After hydrogen uptake ceased, the mixture was filtered through a pad of Celite washing with ethanol (30 mL). The filtrate was concentrated to give 5-[4-(3-(1,1-dimethylethoxy)-3-oxopropyl)phenyl]-2-(1,1-dimethylethyl)-2H-tetrazole (1.2 g, 4.4 mmol) in 78% yield.

Workup

  1. filtrationthe mixture was filtered through a pad of Celite
  2. washwashing with ethanol (30 mL)
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-f2fe1a1a3729496d8098f18f7a098414
Source dataset
uspto-grants-1996_04
Patent number
US05508437

Reaction notes

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