Lithium borohydride → [2-(3-Chloro-phenyl)-2H-tetrazol-5-yl]-methanol

HRID 639775Notes

Reaction equation

HRID 639775 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[N:12]=[N:11][C:10]([CH:13]=[O:14])=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[BH4-].[Li+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[N:12]=[N:11][C:10]([CH2:13][OH:14])=[N:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 59424218HCID 59424218, compound

Product 1

HCID 59424225[2-(3-Chloro-phenyl)-2H-tetrazol-5-yl]-methanolYield 106.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(3-Chloro-phenyl)-2H-tetrazole-5-carbaldehyde (70.8 mg, 0.339 mmol) was dissolved in THF (5 mL) and lithium borohydride (25.9 mg, 1.187 mmol) was added. The reaction was allowed to reflux under argon for three hours and was then allowed to stir overnight at room temperature. The reaction was quenched with 1M hydrochloric acid and an aqueous workup was done extracting with ethyl acetate three times. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated to yield the title compound as a white solid (75.8 mg, 106%). 1H NMR (CDCl3) δ (ppm): 8.190 (s, 1H), 8.070 (m, 1H), 7.507 (m, 2H), 5.082 (s, 2H).

Workup

  1. temperatureto reflux under argon for three hours
  2. customThe reaction was quenched with 1M hydrochloric acid
  3. extractionan aqueous workup was done extracting with ethyl acetate three times
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8a645396c3264dd39f3396c13bc7fbeb
Source dataset
uspto-grants-2010_04
Patent number
US07691892B2

Reaction notes

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