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

HRID 36034Notes

Reaction equation

HRID 36034 reaction equation
[CH3:1][C:2]([N:10]1[N:14]=[N:13][C:12]([C:15]2[CH:20]=[C:19](C=O)[CH:18]=[CH:17][C:16]=2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[N:11]1)([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:3].[BH4-].[Na+].O.[CH2:32]([OH:34])C>>[CH3:3][C:2]([N:10]1[N:14]=[N:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:23]2[CH:28]=[CH:27][C:26]([CH2:32][OH:34])=[CH:25][CH:24]=2)=[N:11]1)([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:1]

Participants

5

Reactant 4

HCID 702EthanolHCID 962WaterHCID 4311764Sodium borohydrideHCID 19939938HCID 19939938, compound

Product 1

HCID 109706982'-[2-(1-methyl-1-phenylethyl)-2H-tetrazol-5-yl]biphenyl-4-methanol

Procedure

A solution of 2,-[2-(1-methyl-1-phenylethyl)-2H-tetrazol-5-yl]biphenyl-4-carbaldehyde (0.62 g, 1.7 mmol), prepared as in Example 8 or 9, and sodium borohydride in 30 mL of absolute ethanol was stirred at room temperature for 1 hour. The mixture poured into 150 mL of water and the mixture was extracted with ethyl acetate. The ethyl acetate layer was dried over magnesium sulfate and then concentrated. The residue was dissolved in approximately 10 mL of absolute diethyl ether and the solution was cooled in an ice bath giving a precipitate. The precipitate was isolated by filtration and drying gave 2'-[2-(1-methyl-1-phenylethyl)-2H-tetrazol-5-yl]biphenyl-4-methanol (0.37 g, 1.0 mmol), m.p. 119°-120° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe ethyl acetate layer was dried over magnesium sulfate
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in approximately 10 mL of absolute diethyl ether
  5. temperaturethe solution was cooled in an ice bath
  6. customgiving a precipitate
  7. customThe precipitate was isolated by filtration
  8. customdrying

Sources & evidence

ORD record
ord-0d1b5a456e6e46b3b3d930edec746710
Source dataset
uspto-grants-1995_05
Patent number
US05412102

Reaction notes

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