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

HRID 1756914
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1756914
[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]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

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

Produkt 1

HCID 21469478(+/-)-2-Dodecyl-alpha-methyl-alpha-phenyl-2H-tetrazole-5-acetic acidAusbeute 1.073,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-d9df3108d5c64ddcb186f3413d73b769
Quelldatensatz
uspto-grants-1995_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05441975

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