Water → 2'-[2-(1-methyl-1-phenylethyl)-2H-tetrazol-5-yl]biphenyl-4-methanol

HRID 1757495

Reaktionsgleichung

Reaktionsgleichung von HRID 1757495
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[C:23]2[N:24]=[N:25][N:26]([C:28]([CH3:36])([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH3:29])[N:27]=2)=[CH:13][CH:12]=1)=O.O.[OH-].[Na+]>C1COCC1>[CH3:36][C:28]([N:26]1[N:25]=[N:24][C:23]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[C:14]2[CH:13]=[CH:12][C:11]([CH2:9][OH:8])=[CH:16][CH:15]=2)=[N:27]1)([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[CH3:29]

Komponenten

6

Edukt 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 118254832'-[2-(1-methyl-1-phenylethyl)-2H-tetrazol-5-yl]biphenyl-4-carboxylic acid methyl esterHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 109706982'-[2-(1-methyl-1-phenylethyl)-2H-tetrazol-5-yl]biphenyl-4-methanolAusbeute 99,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of lithium aluminum hydride (1.9 L, 1M in THF) was cooled to -30° C. and 2'-[2-(1-methyl-1-phenylethyl)-2H-tetrazol-5-yl]biphenyl-4-carboxylic acidmethyl ester (0.848 kg, 2.13 mol), prepared as in Example 3, in 3.5 L of THF was added at a rate such that the reaction temperature remained below -10° C. The mixture was allowed to warm to 0° C. and 77 mL of water, 77 mL of 15% sodium hydroxide and 230 mL of water were sequentially added. The mixture was filtered and the filter cake washed with 3×500 mL of THF. The filtrate was concentrated, then 4 L of hexanes were added and a crystalline product was obtained. The product wasisolated by filtration and the filter cake was washed with hexanes. Drying gave 2'-[2-(1-methyl-1-phenylethyl)-2H-tetrazol-5-yl]biphenyl-4-methanol (0.788 kg, 2.12 mol), m.p. 117°-120° C.

Aufarbeitung

  1. customremained below -10° C
  2. filtrationThe mixture was filtered
  3. washthe filter cake washed with 3×500 mL of THF
  4. concentrationThe filtrate was concentrated
  5. addition4 L of hexanes were added
  6. customa crystalline product was obtained
  7. filtrationThe product wasisolated by filtration
  8. washthe filter cake was washed with hexanes
  9. customDrying

Quellen und Nachweise

ORD-Eintrag
ord-155c8be62e2545e6b8ae52328c6cffd2
Quelldatensatz
uspto-grants-1995_08
Patentnummer
US05446121

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