Methyl iodide → (+/-)-2-Dodecyl-alpha-methyl-alpha-phenyl-2H-tetrazole-5-acetic acid

HRID 1756914Notes

Reaction equation

HRID 1756914 reaction equation
[Li][CH2:2]CCC.[CH2:6]([N:18]1[N:22]=[N:21][C:20]([CH:23]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:24]([OH:26])=[O:25])=[N:19]1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].IC>C1COCC1>[CH2:6]([N:18]1[N:22]=[N:21][C:20]([C:23]([CH3:2])([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:24]([OH:26])=[O:25])=[N:19]1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10523337alpha-(2-Dodecyl-2H-5-tetrazolyl)phenylacetic acid2×HCID 178418339Butyllithium

Product 1

HCID 21469478(+/-)-2-Dodecyl-alpha-methyl-alpha-phenyl-2H-tetrazole-5-acetic acidYield 1,073.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a THF solution (30 mL) of n-BuLi (0.0055 mol, 1.6M in hexanes) at -78° C. under N2 with stirring was added 1.0 g (0.00027 mol) of (±)-2-dodecyl-α-phenyl-2H-tetrazole-5-acetic acid (Compound d, Example 13). The resulting yellow solution was stirred at -78° C. for 30 minutes before iodomethane (0.34 mL, 0.0055 mol) was added. This solution was stirred for 3 hours before quenching with 1N HCl (20 mL). The mixture was then partitioned between ethyl acetate and water. The organic phase was washed with water, brine, dried over MgSO4, filtered, and concentrated in vacuo to yield 1.12 g of pure product.

Workup

  1. additionwas added
  2. custombefore quenching with 1N HCl (20 mL)
  3. customThe mixture was then partitioned between ethyl acetate and water
  4. washThe organic phase was washed with water, brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d9df3108d5c64ddcb186f3413d73b769
Source dataset
uspto-grants-1995_08
Patent number
US05441975

Reaction notes

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