Phenol → Methyl 4-[2'-methoxy-5'-nitro-4'-(phenoxymethyl)phenoxy]butanoate

HRID 533492Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 533492
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:9][C:10]1[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][C:13]([O:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[C:12]([O:27][CH3:28])[CH:11]=1>CO>[CH3:28][O:27][C:12]1[CH:11]=[C:10]([CH2:9][O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][C:13]=1[O:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19]

Komponenten

4

Edukt 2

HCID 996PhenolHCID 21101447Methyl 4-[4'-(bromomethyl)-2'-methoxy-5'-nitrophenoxy]butanoate

Produkt 1

HCID 21101446Methyl 4-[2'-methoxy-5'-nitro-4'-(phenoxymethyl)phenoxy]butanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a suspension of phenol (130 mg, 138 mmol) and methyl 4-[4′-(bromomethyl)-2′-methoxy-5′-nitrophenoxy]butanoate (7) (500 mg, 138 mmol) in anhydrous methanol (5 cm3) was added KtOBu (186 mg, 166 mmol). The resulting green mixture was stirred at r.t. for 30 mins after which time a white precipitate had formed. The precipitate was filtered and recrystallised from methanol affording the desired compound 9 as a pure white solid (319 mg, 61%). m.p. 96-98° C. Found C, 61.0; H, 5.8; N, 4.0; C19H21NO7 requires C, 60.8; H, 5.6; N, 3.7%; Rf 0.64 (SiO2, hexane:EtOAc 2:1 v/v); νmax (KBr disc)/cm−1 3000-2800 (m), 1720 (s), 1610, 1580, 1520, 1280, 1220; δH (300 MHz, CDCl3) 2.21 (2H, q, J=6.7 Hz, CH2), 2.57 (2H, t, J=6.7 Hz, CH2), 3.71 (3H, s, OCH3), 3.91 (3H, s, OCH3), 4.14 (2H, t, J=6.7 Hz, CH2), 5.50 (2H, s, CH2), 6.98-7.02 (3H, m, ar), 7.29-7.34 (3H, m, ar), 7.77 (1H, s, ar) ppm; δC (100 MHz, CDCl3) 24.7 (CH2), 30.4 (CH2), 51.7 (OCH3), 56.3 (OCH3), 67.0 (CH2), 68.2 (CH2), 109.4 (CH), 109.6 (CH), 115.0 (CH), 121.5 (CH), 129.6 (CH), 129.7 (CH), 138.9, 147.0, 154.3, 158.1, 173.2 (COOCH3) ppm; m/z (FAB) 376 [(MH), 20%], 282 [(M-C6H5O), 80%].

Aufarbeitung

  1. additionwas added KtOBu (186 mg, 166 mmol)
  2. customhad formed
  3. filtrationThe precipitate was filtered
  4. customrecrystallised from methanol affording the desired compound 9 as a pure white solid (319 mg, 61%)

Quellen und Nachweise

ORD-Eintrag
ord-3b6fca4ed7794a7d874e9c96bfc12c39
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853270B2

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