Hydrochloric Acid → 2-Chloro-5-(1-tetrazolyl)benzyl alcohol

HRID 1289969Notes

Reaction equation

HRID 1289969 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([N:12]2[CH:16]=[N:15][N:14]=[N:13]2)=[CH:8][C:3]=1[C:4](OC)=[O:5].[BH4-].[Li+].Cl>C1COCC1>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([N:12]2[CH:16]=[N:15][N:14]=[N:13]2)=[CH:8][C:3]=1[CH2:4][OH:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 709876Methyl 2-chloro-5-(1H-tetrazol-1-yl)benzoateHCID 4148881Lithium borohydride

Product 1

HCID 536699762-Chloro-5-(1-tetrazolyl)benzyl alcohol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product from Step B was taken up in 30 mL of THF and 160 mg of lithium borohydride was added. The reaction was stirred for 16 h and was then poured into dilute HCl solution and extracted twice with ethyl acetate. The organic layers were washed with a portion of brine, combined, dried over sodium sulfate and evaporated. When taken up in 50% ethyl acetate in hexanes, the product partially precipitated to give white solid after filtration. The mother liquor was concentrated and additional product was obtained by flash chromatography eluting with 1% HOAc/50% ethyl acetate in hexanes to obtain a total of 400 mg of title compound. T.l.c. (50% ethyl acetate in hexanes) Rf =0.4

Workup

  1. extractionextracted twice with ethyl acetate
  2. washThe organic layers were washed with a portion of brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customthe product partially precipitated
  6. customto give white solid
  7. filtrationafter filtration
  8. concentrationThe mother liquor was concentrated
  9. customadditional product was obtained by flash chromatography
  10. washeluting with 1% HOAc/50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-c5f59710e3114fd7a25f7a37c569c7f6
Source dataset
uspto-grants-1998_05
Patent number
US05750549

Reaction notes

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