Acetone → HCID 19606731, compound

HRID 1603976Notes

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-ff3766e1bfe04eada294c26fe8a6d80d
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05990254

Reaction notes

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