Reaktion #1079966

Reaktionsgleichung

2-adamantylcyclopentadiene

benzophenone

sodium methoxide

→

desired product

Ausbeute 46.8%

3-(2-adamanty)-6,6-diphenylfulvene

Ausbeute 46.8%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.DISSOLUTIONOnce the solids had dissolved
2. 2
   FiltrationThe orange precipitate was collected by suction filtration
3. 3
   workup.STIRRINGthe air dried product was then stirred in 100 methanol for two days before the solid
4. 4
   Filtrationwas collected by suction filtration
5. 5
   Waschenwashed with 100 mL methanol
6. 6
   SonstigeDrying in vacuo for two days

Vorschrift

A 500 mL round bottom flask containing 2-adamantylcyclopentadiene (30.18 g, 150.7 mmol) was added benzophenone (27.50 g, 150.9 mmol) and 300 mL absolute ethanol. Once the solids had dissolved, sodium methoxide (15.00 g, 278 mmol) was added and the reaction was stirred for six days. The orange precipitate was collected by suction filtration and the air dried product was then stirred in 100 methanol for two days before the solid was collected by suction filtration and washed with 100 mL methanol. Drying in vacuo for two days provided 25.72 grams of desired product (46.8%). And second crop was obtained: 6.08 grams (57.9% for both crops). MS (GC-MS) m/z 364.5 (M+). 1H NMR (CDCl3): δ 1.52-2.23 (m, 14H, adamantyl-H), 2.80 (s, 1H, 2-H-adamantyl), 7.30-7.40 (m, 12H, phenyl-H), 6.05 (m, 1H, fulvene-H), 6.29, 6.59 (d, 3JHH=3.4, 3.7 Hz, 2H, fulvene-H). 13C NMR (CDCl3): δ 28.14, 28.14, 31.21, 31.21, 32.72, 32.72, 38.06, 38.92, 38.92 (adamantyl-C), 45.20 (2-C-adamantyl), 118.16, 125.01, 133.10 (fulvene-CH1), 127.68, 127.68, 127.77, 127.77, 128.31, 128.31, 132.02, 132.02, 132.08, 132.08 (phenyl-CH1), 141.70, 141.70 (ipso-C), 144.39, 148.69, 152.27 (fulvene-CH0). Elemental analysis calculated for C28H28: C, 92.26; H, 7.74. Found: C, 83.42; H, 6.59.

Quelle