Hydrochloric Acid → HCID 67326902, compound

HRID 1009688Notes

Reaction equation

HRID 1009688 reaction equation
[CH3:1][CH:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1)[CH2:3][CH2:4][CH:5]=[CH2:6].C([Li])CCC.[C:18]1(=O)[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:20][CH2:19]1.Cl>O1CCCC1>[CH2:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:18]([C:2]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)([CH3:1])[CH2:3][CH2:4][CH:5]=[CH2:6])=[CH:19]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 67351-IndanoneHCID 673274912-(1-Methyl4-pentenyl)pyridineHCID 178418339Butyllithium

Product 1

HCID 67326902HCID 67326902, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 8.95 g (0.0556 mol) of 2-(1-methyl4-pentenyl)pyridine in 50 ml of tetrahydrofuran was cooled to −20° C. and 35 ml of n-butyllithium (15 w.-% in hexane, 0.0556 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 7.33 g of 1-indanone in 8 ml of tetrahydrofuran was then added at such a rate that the temperature remained at 25° C. The mixture was stirred for a further 3 hours and hydrolyzed with 150 ml of dilute hydrochloric acid. The organic phase was separated off, the aqueous phase was extracted once with ethyl acetate, the aqueous phase was subsequently neutralized with aqueous ammonia solution and was extracted three times with 80 ml each time of dichloromethane. The organic phases were combined, dried over magnesium sulfate, the magnesium sulfate was filtered off and the solvent was distilled off. The crude product (about 10 g) was purified by column chromatography using a mixture of hexane:CH2Cl2=1:1 for the separation from starting 2-(1-methyl4-pentenyl)pyridine. Then, a mixture of hexane:CH2Cl2=1:2 was used. This gave 4.81 g (31%) of 2-[1-(1H-inden-3-yl)-1-methyl-4-pentenyl]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 ethyl acetate
  6. extractionwas extracted three times with 80 ml each time of dichloromethane
  7. dry with materialdried over magnesium sulfate
  8. filtrationthe magnesium sulfate was filtered off
  9. distillationthe solvent was distilled off
  10. customThe crude product (about 10 g) was purified by column chromatography
  11. additiona mixture of hexane
  12. customCH2Cl2=1:1 for the separation
  13. additionThen, a mixture of hexane

Sources & evidence

ORD record
ord-1d2022ea9c154e62a382152e03555639
Source dataset
uspto-grants-2011_07
Patent number
US07973114B2

Reaction notes

Loading…