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Potassium Carbonate → 3-(2-Chloro-4-trifluoromethylphenyl)-7-methoxy-4-(4-(2-pyrrolidin-1-yl-ethoxy)-benzyl)-chromen-2-one

HRID 1167814
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Reaktionsgleichung von HRID 1167814
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[C:12]1[C:13](=[O:32])[O:14][C:15]2[C:20]([C:21]=1[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=1)=[CH:19][CH:18]=[C:17]([O:30][CH3:31])[CH:16]=2.Cl.Cl[CH2:35][CH2:36][N:37]1[CH2:41][CH2:40][CH2:39][CH2:38]1.C([O-])([O-])=O.[K+].[K+].[2H]C(Cl)(Cl)Cl.O>CCO.O>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:10])([F:9])[F:11])[CH:5]=[CH:4][C:3]=1[C:12]1[C:13](=[O:32])[O:14][C:15]2[C:20]([C:21]=1[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:35][CH2:36][N:37]3[CH2:41][CH2:40][CH2:39][CH2:38]3)=[CH:25][CH:24]=1)=[CH:19][CH:18]=[C:17]([O:30][CH3:31])[CH:16]=2
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Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 816681-(2-Chloroethyl)pyrrolidine hydrochlorideHCID 120881863-(2-Chloro-4-trifluoromethylphenyl)-4-(4-hydroxybenzyl)-7-methoxychromen-2-oneHCID 131724070CHCl3-H2O

Produkt 1

HCID 120881873-(2-Chloro-4-trifluoromethylphenyl)-7-methoxy-4-(4-(2-pyrrolidin-1-yl-ethoxy)-benzyl)-chromen-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 3-(2-chloro-4-trifluoromethylphenyl)-4-(4-hydroxybenzyl)-7-methoxychromen-2-one (460 mg, 1 mmol), 1-(2-chloroethyl)pyrrolidine hydrochloride (254.7 mg, 1.5 mmol) and K2CO3 (413.9 mg, 2.99 mmol) in EtOH (5 mL) was stirred for 2 min prior to the addition of H2O (0.5 mL). The mixture was stirred at 55° C. for 2.5 h, after which time it was cooled to r.t. and poured into CHCl3—H2O. The layers were separated and the aqueous phase was extracted with CHCl3 (3×). The combined organic layers were washed with brine, dried (MgSO4) and the solvent was removed in vacuo. The resultant brown foam was purified using flash chromatography (silica gel, 19:1 CH2Cl2:MeOH) to provide the title compound as a pale brown foam which displayed: 1H NMR (300 MHz, CD3OD) δ 7.83 (s, 1H), 7.65 (d, 1H, J=9.0 Hz), 7.63 (d, 1H, J=8.0 Hz), 7.51 (d, 1H, J=8.0 Hz), 7.00 (d, 1H, J=2.5 Hz), 6.95 (d, 2H, J=8.5 Hz), 6.89 (dd, 1H, J=2.5, 9.0 Hz), 6.79 (d, 2H, J=8.5 Hz),), 4.07 (d, 1H, J=15.5 Hz), 4.05 (t, 2H, J=5.5 Hz), 3.90 (s, 3H), 3.83 (d, 1H, J=15.5 Hz), 2.89 (t, 2H, J=5.5 Hz), 2.72-2.60 (m, 4H), 1.90-1.75 (m, 4H). MS (ESI) m/z 558 (M+H)+.

Aufarbeitung

  1. stirringThe mixture was stirred at 55° C. for 2.5 h
  2. customThe layers were separated
  3. extractionthe aqueous phase was extracted with CHCl3 (3×)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. customthe solvent was removed in vacuo
  7. customThe resultant brown foam was purified

Quellen und Nachweise

ORD-Eintrag
ord-a153816856f34b61b730736038ffd68c
Quelldatensatz
uspto-grants-2003_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06620838B1

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