Benzaldehyde → Benzothiazol-2-yl-phenyl-methanol

HRID 2404408Notes

Reaction equation

HRID 2404408 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.C([Li])CCC.[CH:15](=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O1CCCC1>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:15]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[OH:22]

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 7222BenzothiazoleHCID 178418339Butyllithium

Product 1

HCID 257798Benzothiazol-2-yl-phenyl-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-20 °C

Procedure

A solution of benzothiazole (1.35 g) in tetrahydrofurane (10 mL) in a dried round bottom baloon is cooled at −70° C. A solution of butyl lithium (4.1 mL) is added and the mixture stirred for 15 minutes. Benzaldehyde (1.03 mL) diluted with tetrahydrofurane (10 mL) is then added. The mixture is stirred at −70° C. for 1 h, allowed to warm to −20° C. and quenched with saturated aqueous ammonium chloride solution. The mixture is extracted with ethyl acetate. Organic extracts are pooled, dried over magnesium sulfate and concentrated under reduced pressure. Trituration of the residue with diisopropyl oxyde affords benzothiazol-2-ylphenylmethanol.

Workup

  1. additionis then added
  2. stirringThe mixture is stirred at −70° C. for 1 h
  3. customquenched with saturated aqueous ammonium chloride solution
  4. extractionThe mixture is extracted with ethyl acetate
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-19108a02a6d44e2ca850634076d4fedc
Source dataset
uspto-grants-2014_08
Patent number
US08802664B2

Reaction notes

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