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

HRID 36033

Reaction equation

[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]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of lithium aluminum hydride (1.9 L, 1 M in THF) was cooled to -30° C. and 2'-[2-(1-methyl-1-phenylethyl)-2H-tetrazol-5-yl]biphenyl-4-carboxylic acid methyl 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 was isolated 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.

Workup

customremained below -10° C
filtrationThe mixture was filtered
washthe filter cake washed with 3×500 mL of THF
concentrationThe filtrate was concentrated
addition4 L of hexanes were added
customa crystalline product was obtained
customThe product was isolated by filtration
washthe filter cake was washed with hexanes
customDrying

Sources & evidence

ORD record: ord-15b06f944d2e4bc784c4e071d8533ca0
Source dataset: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05412102

Linked notes

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