Acetone → HCID 19606731, compound

HRID 726835Notes

Reaction equation

[CH:1]1([C:6]2([CH3:17])[C:14]3[CH2:13][CH:12]=[CH:11][C:10]=3[C:9]([CH3:16])([CH3:15])[CH2:8][CH2:7]2)[CH:5]=[CH:4][CH:3]=[CH:2]1.[CH3:18][C:19]([CH3:21])=O.N1CCCC1>CO>[C:19](=[C:3]1[CH:4]=[CH:5][C:1]([C:6]2([CH3:17])[C:14]3[CH2:13][CH:12]=[CH:11][C:10]=3[C:9]([CH3:16])([CH3:15])[CH2:8][CH2:7]2)=[CH:2]1)([CH3:21])[CH3:18]

Participants

Conditions

Temperature: 0 °C

Procedure

7.70 g (34.0 mmol) of the cyclopentadienyltetrahydroindene (Example 5) are dissolved in 70 ml of methanol and cooled to 0° C. The orange-red reaction solution is subsequently treated successively with 2.96 g (51.0 mmol) of acetone and 4.83 g (68.0 mmol) of pyrrolidine. The mixture is stirred at 0° C. for 5 hours and then, in order to complete the reaction, at room temperature for a further 2 hours, before the reaction is terminated by addition of 4 ml of glacial acetic acid. The red, clear reaction solution is hydrolyzed by means of 200 ml of water, and the yellow suspension is extracted 3× with 50 ml of diethyl ether in each case. Repeated washing of the combined organic phases with saturated, aqueous sodium chloride solution and drying over magnesium sulfate give the fulvene as an orange-red, wax-like residue in a yield of 88% (8.00 g).

Workup

customthe reaction
waitat room temperature for a further 2 hours
custombefore the reaction is terminated by addition of 4 ml of glacial acetic acid
extractionthe yellow suspension is extracted 3× with 50 ml of diethyl ether in each case
washRepeated washing of the combined organic phases with saturated, aqueous sodium chloride solution
dry with materialdrying over magnesium sulfate

Sources & evidence

ORD record: ord-62ea0cdae4364e749c552df386d23766
Source dataset: uspto-grants-1998_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05710297

Reaction notes

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