Tetrabutylammonium Hydroxide → HCID 10908531, compound

HRID 1601883Notes

Reaction equation

HRID 1601883 reaction equation
[CH2:1]1[C:17]2[C:5]([C:6]3[CH:29]=[CH:28][CH:27]=[CH:26][C:7]=3[C:8]3[C:16]=2[CH:15]=[C:14]2[C:9]=3[C:10]3[CH:25]=[CH:24][CH:23]=[CH:22][C:11]=3[C:12]3[CH:21]=[CH:20][CH:19]=[CH:18][C:13]=32)=[CH:4][CH:3]=[CH:2]1.[OH-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH2:48]([O:50][C:51](=[O:70])[C:52]1[CH:57]=[CH:56][C:55]([O:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68]Br)=[CH:54][CH:53]=1)[CH3:49]>O1CCOCC1.C(OCC)C>[CH:18]1[C:13]2[C:12](=[C:11]3[CH:22]=[CH:23][CH:24]=[CH:25][C:10]3=[C:9]3[C:14]=2[CH:15]([CH2:68][CH2:67][CH2:66][CH2:65][CH2:64][CH2:63][CH2:62][CH2:61][CH2:60][CH2:59][O:58][C:55]2[CH:56]=[CH:57][C:52]([C:51]([O:50][CH2:48][CH3:49])=[O:70])=[CH:53][CH:54]=2)[C:16]2[C:8]3=[C:7]3[CH:26]=[CH:27][CH:28]=[CH:29][C:6]3=[C:5]3[CH:4]=[CH:3][CH:2]=[CH:1][C:17]3=2)[CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 2723671Tetrabutylammonium HydroxideHCID 11058114HCID 11058114, compoundHCID 21832273HCID 21832273, compound

Product 1

HCID 10908531HCID 10908531, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 312751,4-DioxaneSolvent2×

Procedure

1H-Tetrabenzo[a,c,g,i]fluorene (13) (2.08 g, 5.68 mmol) was suspended in degassed dioxane 80 mL) and heated to reflux under an atmosphere of nitrogen. Tetrabutylammonium hydroxide (40% w/w in H2O, 3.50 g, 5.41 mmol) was added as a solution in dioxane (20 mL) via syringe which was then washed with dioxane (2×5 mL). A yellow precipitate formed immediately which was filtered under nitrogen and washed with warm dioxane (100 mL) and diethyl ether (100 mL). The salt was resuspended in dioxane (100 mL) and to it added 4-(10-bromo-decyloxy)-benzoic acid ethyl ester (10) (2.08 g, 5.40 mmol). The reaction mixture was refluxed under an atmosphere of nitrogen after which time a dark solution had formed. Solvent was removed in vacuo to form a dark brown oil. This was dissolved in diethyl ether and the supernatant removed to leave a yellow slurry. This was washed with diethyl ether (2×30 mL) and all the diethyl ether extracts combined and concentrated. The resulting residue was purified by flash column chromatography using CH2Cl2 /hexane (1:1) as the eluting solvent. The product was isolated as a pale yellow airy solid which was washed with and concentrated from diethyl ether four times. The desired product was precipitated from diethyl ether as a pale yellow powder (2.46 g, 3.67 mmol, 68%).

Workup

  1. temperatureheated
  2. temperatureto reflux under an atmosphere of nitrogen
  3. washwas then washed with dioxane (2×5 mL)
  4. customA yellow precipitate formed immediately which
  5. filtrationwas filtered under nitrogen
  6. washwashed with warm dioxane (100 mL) and diethyl ether (100 mL)
  7. temperatureThe reaction mixture was refluxed under an atmosphere of nitrogen after which time a dark solution
  8. customhad formed
  9. customSolvent was removed in vacuo
  10. customto form a dark brown oil
  11. customthe supernatant removed
  12. customto leave a yellow slurry
  13. washThis was washed with diethyl ether (2×30 mL) and all the diethyl ether
  14. concentrationconcentrated
  15. customThe resulting residue was purified by flash column chromatography
  16. customThe product was isolated as a pale yellow airy solid which
  17. washwas washed with and
  18. concentrationconcentrated from diethyl ether four times

Sources & evidence

ORD record
ord-5d0f23af0ed240cea7437c57a37468d1
Source dataset
uspto-grants-1999_11
Patent number
US05977400

Reaction notes

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