Boron trifluoride etherate → 7'-Fluoro-3',4'-dihydro-2'H-spiro[[1,3]dithiolane-2,1'-naphthalene]

HRID 919191Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 919191
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2=O)=[CH:4][CH:3]=1.B(F)(F)F.CCOCC.[CH2:22]([SH:25])[CH2:23][SH:24]>>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]32[S:25][CH2:22][CH2:23][S:24]3)=[CH:4][CH:3]=1

Komponenten

4

Edukt 3

HCID 8000Boron trifluoride etherateHCID 109021,2-EthanedithiolHCID 103747647-Fluoro-1,2,3,4-tetrahydronaphthalen-1-one

Produkt 1

HCID 866652417'-Fluoro-3',4'-dihydro-2'H-spiro[[1,3]dithiolane-2,1'-naphthalene]Ausbeute 100 %

Versuchsvorschrift

Dissolved 7-fluorotetralone, 51 (10.0 g, 60.9 mmol) in 1,2-ethanedithiol (10 mL) and cooled reaction to 0° C. Boron trifluoride diethyl etherate (7.5 mL) was added dropwise. The white suspension became yellow and homogenous. The wet ice bath was removed and the reaction was warmed to ambient temperature. The reaction was then diluted with heptanes (25 mL) and poured into an ice cold solution of saturated sodium bicarbonate. The organic layer was separated, dried over sodium sulfate and concentrated to give colorless oil (14.69 g, 60.9 mmol, 100% yield). 1H NMR (400 MHz, CDCl3) δ: 7.60 (d, J=12 Hz, 1H), 6.94 (t, J=4 Hz, 1H), 6.84 (t, J=8 Hz, 1H), 3.56 (m, 2H), 3.46 (m, 2H), 2.75 (m, 2H), 2.37 (m, 2H), 1.99 (m, 2H).

Aufarbeitung

  1. temperaturecooled
  2. customreaction to 0° C
  3. customThe wet ice bath was removed
  4. additionThe reaction was then diluted with heptanes (25 mL)
  5. additionpoured into an ice cold solution of saturated sodium bicarbonate
  6. customThe organic layer was separated
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-704e6a99e18f480d99efc16815b3c75a
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09273009B2

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