Triethylamine → 1,1-dimethylethyl 4-[2-(1,1-dimethylethyl)-2H-tetrazol-5-yl]benzene propenoate

HRID 1721250Notes

Reaction equation

HRID 1721250 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[N:10][N:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[N:12]=2)=[CH:4][CH:3]=1.[C:17]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])(=[O:20])[CH:18]=[CH2:19].C(N(CC)CC)C>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:17]([OH:21])(=[O:20])[CH:18]=[CH2:19].[CH3:23][C:22]([C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[N:10][N:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[N:12]=2)=[CH:4][CH:3]=1)([CH3:25])[CH3:24]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 15458tert-Butyl acrylateHCID 148887285-(4-bromophenyl)-2-(1,1-dimethylethyl)-2H-tetrazole

Product 1

HCID 867465281,1-dimethylethyl 4-[2-(1,1-dimethylethyl)-2H-tetrazol-5-yl]benzene propenoateYield 55%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

A solution of 5-(4-bromophenyl)-2-(1,1-dimethylethyl)-2H-tetrazole (3.0 g, 10.2 mmol), t-butyl acrylate (2.9 mL, 20.4 mmol), and triethylamine (7.9 mL, 59 mmol) in DMF (93 mL) was deoxygenated with argon, whereupon bis(triphenylphosphine)palladium dichloride (0.5 g, 0.8 mmol) was added. After heating at 75° C. for 12 hours the mixture was concentrated under reduced pressure and the brown residue was filtered through a short column of silica gel eluting with a mixture of hexanes and ethyl acetate (9:1). The eluent was concentrated and then purified by chromatography on a Waters Prep 500 liquid chromatograph fitted with two silica gel cartridges eluting with a mixture of hexanes and ethyl acetate (9:1). The fractions containing product were pooled, concentrated and the residue was recrystallized from hexanes to give 1,1-dimethylethyl 4-[2-(1,1-dimethylethyl)-2H-tetrazol-5-yl]benzene propenoate (1.6 g, 5.6 mmol) in 55% yield, mp. 118.5°-120° C.

Workup

  1. additionwas added
  2. concentrationwas concentrated under reduced pressure
  3. filtrationthe brown residue was filtered through a short column of silica gel eluting with a mixture of hexanes and ethyl acetate (9:1)
  4. concentrationThe eluent was concentrated
  5. custompurified by chromatography on a Waters Prep 500 liquid chromatograph
  6. customfitted with two silica gel cartridges
  7. washeluting with a mixture of hexanes and ethyl acetate (9:1)
  8. additionThe fractions containing product
  9. concentrationconcentrated
  10. customthe residue was recrystallized from hexanes

Sources & evidence

ORD record
ord-31007a98a4f049e6a48498da04004d40
Source dataset
uspto-grants-1996_04
Patent number
US05508437

Reaction notes

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