Fluorene → HCID 15045041, compound

HRID 2259274Notes

Reaction equation

[CH:1]1[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C([Li])CCC.Br[CH2:20][CH2:21][CH:22]1[O:26][CH2:25][CH2:24][O:23]1.CCCCCC.C(OCC)(=O)C>C1COCC1>[CH:1]1[C:13]2[CH:12]([CH2:20][CH2:21][CH:22]3[O:26][CH2:25][CH2:24][O:23]3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: -78 °C

Procedure

2-(9-Fluorenyl)ethyl-1,3-dioxolane was prepared from a solution of fluorene (30.0 g, 180.5 mmol) in 400 ml of dry THF cooled in a -78° C. bath under argon, to which was added 100 ml of n-butyllithium (2.0M in cyclohexane) over 15 minutes. After stirring for 0.5 hours at 78° C., 2-(2-bromoethyl)-1,3-dioxolane (22.3 ml, 190 mmol) was added dropwise, and the resulting solution stirred at room temperature for 16 hours. Concentration in vacuo yielded an orange residue which was partitioned between ethyl acetate and saturated ammonium chloride. The organic layer was then washed with brine, dried with magnesium sulfate, and concentrated in vacuo to afford an orange oil. Flash chromatography on silica, hexane:ethyl acetate 20:1 to 1:1 yielded a yellow oil (36.38 g, 76%).

Workup

stirringthe resulting solution stirred at room temperature for 16 hours
concentrationConcentration in vacuo
customyielded an orange residue which
customwas partitioned between ethyl acetate and saturated ammonium chloride
washThe organic layer was then washed with brine
dry with materialdried with magnesium sulfate
concentrationconcentrated in vacuo
customto afford an orange oil

Sources & evidence

ORD record: ord-18f89ec8e2d2459d9f40aac52b409996
Source dataset: uspto-grants-1995_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05472973

Reaction notes

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