Methane → HCID 9940747, compound

HRID 1601886Notes

Reaction equation

HRID 1601886 reaction equation
[CH:1]1[C:17]2[C:5](=[C:6]3[CH:48]=[CH:47][CH:46]=[CH:45][C:7]3=[C:8]3[C:16]=2[CH:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][O:28][C:29]2[CH:34]=[CH:33][C:32]([CH2:35][OH:36])=[CH:31][CH:30]=2)[C:14]2[C:9]3=[C:10]3[CH:44]=[CH:43][CH:42]=[CH:41][C:11]3=[C:12]3[CH:40]=[CH:39][CH:38]=[CH:37][C:13]3=2)[CH:4]=[CH:3][CH:2]=1.C([O:51][C:52](=O)[CH2:53][C:54](=[O:64])[C:55]1[CH:60]=[C:59]([F:61])[C:58]([F:62])=[CH:57][C:56]=1[F:63])C.C.CO>CN(C1C=CN=CC=1)C.C1(C)C=CC=CC=1.C(Cl)Cl.CO>[F:63][C:56]1[CH:57]=[C:58]([F:62])[C:59]([F:61])=[CH:60][C:55]=1[C:54](=[O:64])[CH2:53][C:52]([O:36][CH2:35][C:32]1[CH:31]=[CH:30][C:29]([O:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH:15]2[C:14]3[C:9](=[C:10]4[CH:44]=[CH:43][CH:42]=[CH:41][C:11]4=[C:12]4[CH:40]=[CH:39][CH:38]=[CH:37][C:13]4=3)[C:8]3[C:16]2=[C:17]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]2=[C:6]2[CH:48]=[CH:47][CH:46]=[CH:45][C:7]2=3)=[CH:34][CH:33]=1)=[O:51]

Participants

8

Reactant 4

HCID 297MethaneHCID 887MethanolHCID 2758933Ethyl 2,4,5-trifluorobenzoylacetateHCID 10930203HCID 10930203, compound

Product 1

HCID 9940747HCID 9940747, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

4-[[10-(17H-Tetrabenzo[a,c,g,i]fluoren-17-yl)decyl]oxy]benzenemethanol (8) (44.9 mg, 0.071 mmol) and DMAP (3.2 mg, 0.026 mmol) were added to an oven-dried flask and dissolved in freshly distilled toluene (8 mL). 3-Oxo-3-(2,4,5-trifluoro-phenyl)-propionic acid ethyl ester (7) (46.2 mg, 0.19 mmol) was added and the resultant solution refluxed under an atmosphere of nitrogen for 20 hours. The reaction was cooled to room temperature and solvent removed in vacuo to yield an orange oil. This was dissolved in DCM/methanol (3:2, 25 mL). Charcoal (prewashed with toluene, 510 mg) was added and the suspension stirred at room temperature for 15 minutes. Methanol was added in portions (total 45 mL) and stirring continued until TLC analysis showed that none of the desired product was present in the supernatant liquid. The supernatant was removed by centrifugation and the charcoal residue then suspended in toluene (40 mL). The suspension was then stirred at 40° C. for 15 minutes and the supernatant removed by centrifugation. This was repeated with fresh toluene until no fluorescent products were detected in the supernatant by TLC. The toluene washes were combined and solvent removed in vacuo. The yellow residue was purified by flash column chromatography using DCM as eluent to yield the desired product (35.2 mg, 60%).

Workup

  1. customsolvent removed in vacuo
  2. customto yield an orange oil
  3. stirringstirring

Sources & evidence

ORD record
ord-fc7feca8a0954ef18a1735465d60b4b3
Source dataset
uspto-grants-1999_11
Patent number
US05977400

Reaction notes

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