Acetic Acid → 2-[2-(1H-inden-3-yl)ethyl]pyridine

HRID 1983806Notes

Reaction equation

[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1)=[CH2:2].[CH2:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10]1.CC(C)([O-])C.[K+].C(O)(=O)C>C1(C)C=CC=CC=1>[CH2:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([CH2:2][CH2:1][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=2)=[CH:10]1

Participants

Conditions

Temperature: 115 °C

Procedure

43 g (0.47 mol) of 2-vinylpyridine were added to a mixture of 56 ml (0.48 mol) of indene in 40 ml of toluene and 4 g (0.036 mol) of solid potassium tert-butoxide at 60-90° C. over a period of 40 minutes. The mixture was then stirred for another 2 hours at 115° C., cooled to room temperature and subsequently neutralized by means of 2 ml of glacial acetic acid. Insoluble constituents were filtered off and the filtrate was distilled under reduced-pressure. This gave 42 g of 2-[2-(1H-inden-3-yl)ethyl]pyridine (40%, b.p. 161-163° C. at 2 mm).

Workup

temperaturecooled to room temperature
filtrationInsoluble constituents were filtered off
distillationthe filtrate was distilled under reduced-pressure

Sources & evidence

ORD record: ord-2f13233ead1145d69777dc621542ec3e
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07541481B2

Reaction notes

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