Water → 3,3'-(2-Phenylethene-1,1-diyl)bis((trifluoromethoxy)benzene)

HRID 1712786

Reaktionsgleichung

Reaktionsgleichung von HRID 1712786
[H-].[Na+].[F:3][C:4]([F:26])([F:25])[O:5][C:6]1[CH:7]=[C:8]([C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][C:21]([F:24])([F:23])[F:22])[CH:15]=2)=O)[CH:9]=[CH:10][CH:11]=1.[CH2:27](P(=O)(OCC)OCC)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.O>C1COCC1.C1OCCOCCOCCOCCOC1>[C:28]1([CH:27]=[C:12]([C:14]2[CH:15]=[C:16]([O:20][C:21]([F:24])([F:23])[F:22])[CH:17]=[CH:18][CH:19]=2)[C:8]2[CH:7]=[C:6]([O:5][C:4]([F:26])([F:25])[F:3])[CH:11]=[CH:10][CH:9]=2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 14122Diethyl benzylphosphonateHCID 24758Sodium hydrideHCID 59458637Bis(3-(trifluoromethoxy)phenyl)methanone

Produkt 1

HCID 594586043,3'-(2-Phenylethene-1,1-diyl)bis((trifluoromethoxy)benzene)Ausbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3633615-Crown-5KatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a suspension of NaH (60% in oil, 0.24 g, 6 mmol) in dry THF (25 mL) under nitrogen was added 15-crown-5 (0.06 g). The suspension was cooled in an ice bath. Bis(3-(trifluoromethoxy)phenyl)methanone (2.10 g, 6 mmol) and diethyl benzylphosphonate (1.37 g, 6 mmol) were dissolved in THF (12 mL) and added to the suspension. The reaction mixture was stirred at ice bath temperature for 15 min, allowed to warm to rt and stirred overnight. The reaction mixture was poured into water and extracted with ether (2×). The combined ether layers were washed with 10% NaHSO3, sat. NaCl, dried over K2CO3, filtered and purified by ISCO using a gradient of 0-4% EtOAc/hexanes as eluent to give 3,3′-(2-phenylethene-1,1-diyl)bis((trifluoromethoxy)benzene) as a colorless oil (1.34 g, 53% yield). 1H NMR (400 MHz, CDCl3) δ ppm 7.33 (m, 2H), 7.2-7.1 (m, 8H), 7.04 (s, 1H), 7.0-6.97 (m, 3H).

Aufarbeitung

  1. temperatureThe suspension was cooled in an ice bath
  2. additionadded to the suspension
  3. stirringstirred overnight
  4. extractionextracted with ether (2×)
  5. washThe combined ether layers were washed with 10% NaHSO3, sat. NaCl
  6. dry with materialdried over K2CO3
  7. filtrationfiltered
  8. custompurified by ISCO

Quellen und Nachweise

ORD-Eintrag
ord-f3bfa1f54127444a8fee4c4e1fa6e775
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07790770B2

Verknüpfte Notizen

Wird geladen…