Hydrochloric Acid → HCID 67326808, compound

HRID 1009685Notes

Reaction equation

HRID 1009685 reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[C:19]1(=O)[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:21][CH2:20]1.Cl>C(OCC)C>[CH2:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[CH2:1][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:20]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 67351-IndanoneHCID 75812-(Phenylmethyl)pyridineHCID 178418339Butyllithium

Product 1

HCID 67326808HCID 67326808, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-20 °C

Procedure

A mixture of 3.23 ml (0.02 mol) of 2-benzylpyridine in 15 ml of diethyl ether was cooled to −20° C. and 13 ml of n-butyllithium (1.6M in hexane, 0.02 mol) were subsequently added while stirring. The mixture was allowed to come to room temperature, stirred for another one hour and subsequently cooled to −60° C. A solution of 2.8 g (0.021 mol) of 1-indanone in 10 ml of diethyl ether was subsequently added while maintaining the temperature. The mixture was allowed to warm to room temperature, stirred for a further 3.5 hours and hydrolyzed with 40 ml of dilute hydrochloric acid. The solid which had precipitated was filtered off, the organic phase was separated off and the aqueous phase was extracted twice with ethyl acetate. The aqueous phase was then neutralized with aqueous ammonia solution and extracted three times with 30 ml each time of methylene chloride. The organic phases were combined, dried over magnesium sulfate, the magnesium sulfate was filtered off and the solvent was distilled off. Recrystallization of the residue obtained in this way from hexane gave 1.9 g (34%) of [2-(1H-inden-3-yl)(phenyl)methyl]pyridine.

Workup

  1. customto come to room temperature
  2. stirringstirred for another one hour
  3. temperaturesubsequently cooled to −60° C
  4. temperaturewhile maintaining the temperature
  5. temperatureto warm to room temperature
  6. customThe solid which had precipitated
  7. filtrationwas filtered off
  8. customthe organic phase was separated off
  9. extractionthe aqueous phase was extracted twice with ethyl acetate
  10. extractionextracted three times with 30 ml each time of methylene chloride
  11. dry with materialdried over magnesium sulfate
  12. filtrationthe magnesium sulfate was filtered off
  13. distillationthe solvent was distilled off
  14. customRecrystallization of the residue
  15. customobtained in this way from hexane

Sources & evidence

ORD record
ord-e107ecfd610e4766944a3dac0465f3cb
Source dataset
uspto-grants-2011_07
Patent number
US07973114B2

Reaction notes

Loading…