Hydrochloric Acid → 2-[1-(1H-inden-3-yl)-1-methylethyl]pyridine

HRID 1983867Notes

Reaction equation

HRID 1983867 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1)([CH3:3])[CH3:2].C([Li])CCC.[C:15]1(=O)[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:17][CH2:16]1.Cl>O1CCCC1>[CH2:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:15]([C:1]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=2)([CH3:3])[CH3:2])=[CH:16]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 67351-IndanoneHCID 695232-IsopropylpyridineHCID 178418339Butyllithium

Product 1

HCID 121357382-[1-(1H-inden-3-yl)-1-methylethyl]pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 10.8 g (0.09 mol) of 2-isopropylpyridine in 47 ml of tetrahydrofuran was cooled to −20° C. and 62.5 ml of n-butyllithium (1.6M in hexane, 0.11 mol) were subsequently added while stirring. The mixture was allowed to come to room temperature and was stirred for a further one hour. A solution of 15.84 g (0.12 mol) of 1-indanone in 12 ml of tetrahydrofuran was then added at such a rate that the temperature remained at 25° C. The mixture was stirred for a further 12 hours and hydrolyzed with 200 ml of dilute hydrochloric acid. The organic phase was separated off, the aqueous phase was extracted once with diethyl ether, the aqueous phase was subsequently neutralized with aqueous ammonia solution and was extracted three times with 100 ml each time of chloroform. The organic phases were combined, dried over magnesium sulfate, the magnesium sulfate was filtered off and the solvent was distilled off. This gave 16.6 g (77%) of 2-[1H-inden-3-yl)-1-methylethyl]pyridine.

Workup

  1. customto come to room temperature
  2. stirringwas stirred for a further one hour
  3. customremained at 25° C
  4. customThe organic phase was separated off
  5. extractionthe aqueous phase was extracted once with diethyl ether
  6. extractionwas extracted three times with 100 ml each time of chloroform
  7. dry with materialdried over magnesium sulfate
  8. filtrationthe magnesium sulfate was filtered off
  9. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-c9fc9f1c8ed240bc8dfcc3228f6b7547
Source dataset
uspto-grants-2009_06
Patent number
US07541473B2

Reaction notes

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