Diethyl Ether → HCID 12997994, compound

HRID 1866795Notes

Reaction equation

C(OCC)C.Br[C:7]1[C:11](OC)([CH3:12])[CH2:10][CH2:9][C:8]=1[CH3:15].C([Li])CCC.[CH:21](=[C:25]1[CH:29]=[CH:28][CH:27]=[CH:26]1)[CH2:22][CH2:23][CH3:24]>O>[C:25]1([CH:21]([C:7]2[C:11]([CH3:12])=[CH:10][CH2:9][C:8]=2[CH3:15])[CH2:22][CH2:23][CH3:24])[CH:26]=[CH:27][CH2:28][CH:29]=1

Participants

Conditions

Temperature: -30 °C

Procedure

15 ml of diethylether was added to 2-bromo-3-methoxy-1,3-dimethyl-cyclopentene (2 g, 9.75 mmol), and the result was cooled to −30° C. Then, n-butyllithium (2.7 g, 9.75 mmol) was added and the reactant solution was incubated at an elevated temperature for 15 minutes and again cooled to −30° C. Then, 1 eq. (1.3 g) of the 5-butylidene-cyclopenta-1,3-diene prepared in (1-1) was added, and the result was incubated for 3 hours. Then, 15 ml of diethylether and 15 ml of water were added, and the resultant solution was washed with 30 ml of 1 N HCl for 3 minutes and neutralized with 30 ml of an aqueous saturated sodium bicarbonate solution. An organic layer was separated, dried over magnesium sulfate to remove water and then subjected to solvent removal in a rotary evaporator. The resultant residue was purified through silica-based column chromatography (hexane) to give 2-(1-cyclopenta-1,4-dienylbutyl)-1,3-dimethylcyclopenta-1,3-diene (yield: 65%).

Workup

temperatureagain cooled to −30° C
additionwas added
waitthe result was incubated for 3 hours
washthe resultant solution was washed with 30 ml of 1 N HCl for 3 minutes
customAn organic layer was separated
dry with materialdried over magnesium sulfate
customto remove water
customsubjected to solvent removal in a rotary evaporator
customThe resultant residue was purified through silica-

Sources & evidence

ORD record: ord-c9e2185736904ad8b90df1824a79fffc
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07629481B2

Reaction notes

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