tert-Butyl (triphenylphosphoranylidene) acetate → HCID 67412080, Verbindung

HRID 1526419Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1526419
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:15]2[N:14]3[CH2:18][CH2:19][C:20](=O)[C:13]3=[CH:12][C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22]([O:26][C:27](=[O:48])[CH:28]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([CH3:25])([CH3:24])[CH3:23]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:15]2[N:14]3[CH2:18][CH2:19]/[C:20](=[CH:28]\[C:27]([O:26][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:48])/[C:13]3=[CH:12][C:11]=2[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 256127tert-Butyl (triphenylphosphoranylidene) acetate2×HCID 216859796-Phenylmethoxy-1,2-dihydropyrrolo[1,2-a]indol-3-one

Produkt 1

HCID 67412080HCID 67412080, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 7-(benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-one (20.0 g, 72.1 mmol) and tert-Butyl(triphenylphosphoranylidene)acetate (136 g, 361 mmol) in THF (700 mL) was heated at reflux for 4 days. Additional and tert-Butyl(triphenylphosphoranylidene)acetate (27.1 g, 72.1 mmol) was added and stiffing at reflux was continued for an additional 24 h. The mixture was cooled to room temperature and the solvent was removed under reduced pressure. Recrystallization from hot IPA gave (E)-tert-butyl 2-(7-(benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-ylidene)acetate as a white solid. Exact mass calculated for C24H25NO3: 375.2, found: LCMS m/z=376.2, (M+H+); 1H NMR (400 MHz, CDCl3) δ ppm 1.53 (s, 9 H), 3.75 (td, J1=6.4, J2=2.4 Hz, 2 H), 4.20 (t, J=6.4 Hz, 2 H), 5.11 (s, 2 H), 6.23 (t, J=2.4 Hz, 1 H), 6.58 (s, 1 H), 6.98 (dd, J1=8.9, J2=2.3 Hz, 1 H), 7.13 (d, J=2.3 Hz, 1 H), 7.21 (d, J=8.9 Hz, 1 H), 7.33 (m, 1 H), 7.39 (m, 2 H), 7.48 (m, 2 H).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 4 days
  3. temperatureat reflux
  4. customthe solvent was removed under reduced pressure
  5. customRecrystallization from hot IPA

Quellen und Nachweise

ORD-Eintrag
ord-f0a7db00c54b447d9482870c93a2be48
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09085581B2

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