Methyl Ethyl Ketone → HCID 68843936, compound

HRID 2116925Notes

Reaction equation

HRID 2116925 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

3

Reactant 2

HCID 6569Methyl Ethyl Ketone3×HCID 8418Anthracene

Product 1

HCID 68843936HCID 68843936, compound

Procedure

A suspension of 2,7-Bis(diethylphosphonatomethyl)-9,9-dipropylfluorene (4) (2.15 g, 4.0 mmol), 3,4,5-trimethoxybenzaldehyde (5) (1.76 g, 9.0 mmol), and potassium hydroxide (0.75 g, 13 mmol) in THF (20 mL) and DMSO (1 mL) was heated at 70° C. for 4 hours. The suspension was diluted with Ethanol (50 mL) and the solvent removed under vacuum. The product was purified by refluxing in Methanol followed by filtration. After drying, (II-1) was obtained as a pale yellow powder (1.90 g, 76%). The UV/VIS spectrum of (II-1) in methyl ethyl ketone (MEK) has two maxima at 380 nm and at 399 nm with a molar extinction coefficient of 89724 Mol−1 cm−1 and 72301 Mol−1 cm−1 respectively. Under UV irradiation in MEK, (II-1) shows a strong blue fluorescence with fluorescence peaks at 417 nm and 439 nm. The fluorescence quantum yield of (II-1) relative to the anthracene standard is 0.65 (in MEK solvent, not degassed). The 1H-NMR data in CDCl3 are summarized in table 1; in the table s means singlet, d means doublet, dd means double doublet, m means multiplet and J means the coupling constant.

Workup

  1. customnot degassed)

Sources & evidence

ORD record
ord-3a1240e0bbd64a319d280ef12abe61ba
Source dataset
uspto-grants-2008_10
Patent number
US07439537B2

Reaction notes

Loading…