Vinyl Acetate → (1R)-1-[2-(3-Methylphenyl)-2H-tetrazol-5-yl]ethyl acetate

HRID 2422729Notes

Reaction equation

HRID 2422729 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N:8]2[N:12]=[N:11][C:10]([CH:13]([OH:15])[CH3:14])=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[C:16](OC=C)(=[O:18])[CH3:17]>C1(C)C=CC=CC=1>[C:16]([O:15][C@@H:13]([C:10]1[N:11]=[N:12][N:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[CH:3]=2)[N:9]=1)[CH3:14])(=[O:18])[CH3:17]

Participants

4

Reactant 2

HCID 7904Vinyl AcetateHCID 248533921-[2-(3-Methylphenyl)-2H-tetrazol-5-yl]ethanol

Product 1

HCID 25264100(1R)-1-[2-(3-Methylphenyl)-2H-tetrazol-5-yl]ethyl acetateYield 42.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 1-[2-(3-methylphenyl)-2H-tetrazol-5-yl]ethanol (93 g, 460 mmol) and Novozyme 435® (10 g) in dry toluene (4800 mL) was stirred slowly. Vinyl acetate (39.2 g, 460 mmol) was added and the mixture was stirred at room temperature for 5 hours. Novozyme 435® was filtrated and washed with toluene (100 mL). The filtrate was concentrated and purified on silica using petroleum ether/ethyl acetate (6:1) as eluent giving the title product (47.92 g, 42%).

Workup

  1. stirringthe mixture was stirred at room temperature for 5 hours
  2. filtrationNovozyme 435® was filtrated
  3. washwashed with toluene (100 mL)
  4. concentrationThe filtrate was concentrated
  5. custompurified on silica

Sources & evidence

ORD record
ord-3c9f6e02fcae42d6a2f6315f501c57e1
Source dataset
uspto-grants-2011_06
Patent number
US07960422B2

Reaction notes

Loading…