Methyl Ethyl Ketone → HCID 68843936, compound
Reaction equation
[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12](C=2)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.[CH2:15]([C:17]([CH3:19])=O)[CH3:16]>>[CH:15]([C:17]1[CH:19]=[CH:1][C:14]2[C:8]3[C:7](=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH2:6][C:5]=2[C:4]=1[CH:3]=[CH2:2])=[CH2:16]Participants
Procedure
To a solution of 2,7-Bis(diethylphosphonatomethyl)-9,9-dipropylfluorene (4) (26.8 g) and 3,5-dimethoxy-4-(1-methylpropoxy)-benzaldehyde (6) (26.2 g) in tetrahydrofuran (200 mL) was added potassium hydroxide (8.4 g) and dimethylsulfoxide (5.0 mL). The suspension was stirred at 70° C. for 4 hours and then isopropanol (150 mL) was added. The solvent of the supernatant solution was removed at reduced pressure and the resultant oil was stirred in methanol (200 mL). The precipitate was filtered off and purified by stirring in boiling ethanol (200 mL) two times. After drying, (II-2) was obtained as a pale yellow powder (25.8 g, 72%). The UV/VIS spectrum of (II-2) in methyl ethyl ketone (MEK) has two maxima at 382 nm and at 402 nm with a molar extinction coefficient of 93092 Mol−1 cm−1 and 75139 Mol−1 cm−1 respectively. Under UV irradiation in MEK, (II-2) shows a strong blue fluorescence with fluorescence peaks at 419 nm and 444 nm. The fluorescence quantum yield of (II-2) relative to the anthracene standard is 0.66 (in MEK solvent, not degassed). The 1H-NMR data in CDCl3 are summarized in table 2.
Workup
- customnot degassed)
Sources & evidence
- ORD record
- ord-bc02b57e4fdf4e848f1df8a612bf32b0
- Source dataset
- uspto-grants-2008_10
- Patent number
- US07439537B2
Reaction notes
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