Water → {2'-[1-(Triphenylmethyl)-1H-tetrazol-5-yl][1,1'-biphenyl]-4-yl}methanol

HRID 1081860Notes

Reaction equation

HRID 1081860 reaction equation
C([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]2[N:22]([C:23]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:21]=[N:20][N:19]=2)=[CH:8][CH:7]=1)(=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].O>C1COCC1>[OH:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]2[N:22]([C:23]([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:21]=[N:20][N:19]=2)=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 15114592HCID 15114592, compoundHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 15114593{2'-[1-(Triphenylmethyl)-1H-tetrazol-5-yl][1,1'-biphenyl]-4-yl}methanolYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3.4 g of 4-(acetoxymethyl)-2'-(1-triphenylmethyltetrazol-5-yl)biphenyl dissolved in 30 ml of anhydrous THF, are dropped during 0.5h into a suspension of 0.5 g of LiAlH4 in 20 ml of anhydrous THF at 0° C. The mixture is stirred for 24h at 0° C., then a stoichiometric amount of water is added to decompose LiAlH4 and the precipitated salts are filtered off. The solution is evaporated and the residue is triturated with an hexane:ethyl acetate mixture (9:1). Upon filtration and drying, 2.6 g of a white powder are obtained (Yield: 83%).

Workup

  1. filtrationthe precipitated salts are filtered off
  2. customThe solution is evaporated
  3. customthe residue is triturated with an hexane
  4. filtrationUpon filtration
  5. customdrying

Sources & evidence

ORD record
ord-133734a6e9c842d5b323b6b0de1cdbc6
Source dataset
uspto-grants-1996_12
Patent number
US05587390

Reaction notes

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