Ethylene Glycol → 5'-Bromospiro[1,3-dioxolane-2,3'-[3H]indol]-2'(1'H)-one

HRID 1052952

Reaktionsgleichung

Reaktionsgleichung von HRID 1052952
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[O:12].[CH2:13](O)[CH2:14][OH:15].CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]12[O:15][CH2:14][CH2:13][O:12]1

Komponenten

5

Edukt 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 68895-Bromoisatin

Produkt 1

HCID 27329225'-Bromospiro[1,3-dioxolane-2,3'-[3H]indol]-2'(1'H)-oneAusbeute 87,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A magnetically stirred solution of 5-bromoindoline-2,3-dione (226 g, 1.0 mol, 1 eq.), ethylene glycol (186 g, 3.0 mol, 3 eq.), p-TSA (30 g, 0.16 mol, 16 mol %) and toluene (1500 mL) was refluxed overnight using a Dean-Stark apparatus. After total consumption of 5-bromoindoline-2,3-dione, EtOAc (1500 mL) and water (1000 mL) were added to remove excess of diol. The aqueous layer was extracted twice with EtOAc (500 mL). The collected organic layers were collected, dried over Na2SO4, filtered and concentrated under reduced pressure. The yellowish solid was washed with diethyl ether to give the desired compound as a pale yellow solid (236 g, 87%). 1H NMR (400 MHz, DMSO-d6): δH 10.56 (s, 1H), 7.31-7.33 (m, 2H), 6.93 (d, J=8.0 Hz, 1H), 4.27-4.35 (m, 4H), 2.35 (s, 3H), 2.18 (s, 3H). MS (ESI) m/e [M+1]+ 270, 272.

Aufarbeitung

  1. customAfter total consumption of 5-bromoindoline-2,3-dione, EtOAc (1500 mL) and water (1000 mL)
  2. additionwere added
  3. customto remove excess of diol
  4. extractionThe aqueous layer was extracted twice with EtOAc (500 mL)
  5. customThe collected organic layers were collected
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. washThe yellowish solid was washed with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-d6519d0f762d455da3d0504d66c1d37f
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09393232B2

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