Benzaldehyde → Diisopropyl Ether

HRID 572820Notes

Reaction equation

HRID 572820 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[CH2:10]([Li])[CH2:11][CH2:12]C.[CH:15](=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O1CCCC1>[CH:11]([O:22][CH:9]([CH3:8])[CH3:4])([CH3:12])[CH3:10].[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

6

Reactant 3

HCID 240BenzaldehydeHCID 7222BenzothiazoleHCID 178418339Butyllithium

Product 2

HCID 7914Diisopropyl EtherHCID 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 balloon 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 oxide 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-a26dd57dca6a4cd4be961b63d2cc5f84
Source dataset
uspto-grants-2015_05
Patent number
US09029357B2

Reaction notes

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