Pyridine → HCID 66779249, Verbindung

HRID 2382246Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2382246
[CH2:1]([O:5][C:6]1[CH:36]=[CH:35][C:9]2[C:10]3[C:27]4([O:32][CH2:31][C:30]([CH3:34])([CH3:33])[CH2:29][O:28]4)[C:11]=3[C:12]3[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][OH:26])=[CH:16][C:13]=3[CH2:14][CH2:15][C:8]=2[CH:7]=1)[CH2:2][CH2:3][CH3:4].N1C=CC=CC=1.Cl[C:44]([O:46][C:47]1[CH:52]=[CH:51][C:50]([N+:53]([O-:55])=[O:54])=[CH:49][CH:48]=1)=[O:45]>C(Cl)Cl>[C:44](=[O:45])([O:46][C:47]1[CH:48]=[CH:49][C:50]([N+:53]([O-:55])=[O:54])=[CH:51][CH:52]=1)[O:26][CH2:25][CH2:24][O:23][CH2:22][CH2:21][O:20][C:17]1[CH:18]=[CH:19][C:12]2[C:11]3[C:27]4([O:32][CH2:31][C:30]([CH3:34])([CH3:33])[CH2:29][O:28]4)[C:10]=3[C:9]3[CH:35]=[CH:36][C:6]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])=[CH:7][C:8]=3[CH2:15][CH2:14][C:13]=2[CH:16]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 821294-Nitrophenyl chloroformateHCID 667789362-{2-[(9-Butoxy-5',5'-dimethyl-6,7-dihydrospiro-[dibenzo[a,e]cyclopropa[c][8]annulene-1,2'-[1,3]dioxan]-4-yl)oxy]ethoxy}ethanol

Produkt 1

HCID 66779249HCID 66779249, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of alcohol 11 (0.439 g, 0.89 mmol) and pyridine (0.25 g, 3.21 mmol) in CH2Cl2 (approximately 5 mL) was added to a solution of 4-nitrophenyl chloroformate (0.30 g, 1.49 mmol) in CH2Cl2 (25 mL) at room temperature, and the reaction mixture was stirred for 20 minutes at room temperature. Solvent was evaporated under reduced pressure, and the residue was separated by chromatography (Hex:ExOAc 4:1+1.5% of Et3N) to provide 0.317 g (0.48 mmol 80%) of 12 as and 0.113 g (0.23 mmol) of starting 11. 1H NMR: 8.25 (d, J=8.8 Hz, 2H) 7.65 (dd, J=8.4, 2.0 Hz, 2H), 7.35, (d, J=9.2, 2H), 6.92-6.82 (m, 4H), 4.43 (t, J=4.4 Hz, 2H), 4.19 (t, J=6.4 Hz, 2H), 3.98 (t, J=4.4 Hz, 2 H), 3.92 (m, 7H), 3.22 (d, J=10.8 Hz, 2H), 2.43 (d, J=10.8 Hz, 2H), 1.75 (p, J=7.2 Hz, 2H), 1.51 (six, J=7.6 Hz, 2H), 1.21 (s, 3H), 1.19 (s, 3H), 0.98 (t, J=7.2 Hz, 3H); 13C NMR: 159.9, 159.2, 155.7, 152.7, 150.0 147.4, 145.6, 131.77, 131.63, 125.5, 124.6, 123.4, 122.0, 119.8, 119.1, 116.25, 116.19, 112.2, 112, 15, 84.1, 79.4, 70.0, 69.1, 68.4, 70.0, 67.8, 37.1, 31.5, 30.8, 22.87, 22.79, 19.5, 14.1.

Aufarbeitung

  1. customSolvent was evaporated under reduced pressure
  2. customthe residue was separated by chromatography (Hex:ExOAc 4:1+1.5% of Et3N)

Quellen und Nachweise

ORD-Eintrag
ord-121656ef26214b1d8c0b412d709bb400
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08258347B2

Notizen zur Reaktion

Wird geladen…