Phthalaldehyde → 1-Methoxy-3-(1-nitrocyclopentyl)-1,3-dihydroisobenzofuran

HRID 1737313

Reaktionsgleichung

Reaktionsgleichung von HRID 1737313
[N+](C1CCCC1)([O-])=O.C1C=C(C=O)C(C=O)=CC=1.C[O-].[Na+].[CH3:22][O:23][CH:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]([C:33]2([N+:39]([O-:41])=[O:40])[CH2:38]C[CH2:36][CH2:35][CH2:34]2)[O:25]1>CO>[CH3:22][O:23][CH:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]([C:33]2([N+:39]([O-:41])=[O:40])[CH2:38][CH2:36][CH2:35][CH2:34]2)[O:25]1

Komponenten

6

Edukt 4

HCID 4807PhthalaldehydeHCID 75714NitrocyclopentaneHCID 10942334Sodium MethoxideHCID 218427081-Methoxy-3-(1-nitrocyclohexyl)-1,3-dihydroisobenzofuran

Produkt 1

HCID 218427051-Methoxy-3-(1-nitrocyclopentyl)-1,3-dihydroisobenzofuran

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Condensation of nitrocyclopentane (5.00 g, 40.0 mmol) with o-phthalaldehyde (3.76 g, 28.0 mmol) in the presence of freshly prepared sodium methoxide (10 mmol) in MeOH is carried out as described above for compound a. The resulting pale green oil (7.21 g, 98%) is pure enough for use in the next step. The following data were obtained on a ca. 1:1 mixture of the cis and trans diastereoisomers. 1H NMR (CDCl3) 7.50-7.25 (m, 3), 7.10-7.00 (m, 1), 6.16 and 5.91 (isomer I, 2 d, 1 total, J=2.3), 5.93 and 5.80 (isomer II, s and d, respectively, 1 total, J=0.7 Hz), 3.49 and 3.30 (isomers I and II, respectively, 2 s, 3 total), 2.50-2.35 (m, 1), 2.30-1.90 (m, 3), 1.75-1.50 (m, 4); IR (film) 1543, 1464, 1398, 1373, 1348, 1113, 1094, 1026, 974, 756; MS (CI/CH4, eE=120 eV), m/z 236 (M-H)+, 219, 206, 191, 175, 159, 149 (base peak), 131, 118, 91, 73; Anal. Calcd for C12H15NO2 (MW=237.3): C, 60.75; H, 6.37; N, 5.90. Found: C, 60.48; H, 6.28; N, 6.00.

Aufarbeitung

  1. customThe following data were obtained on a ca. 1:1 mixture of the cis and trans diastereoisomers

Quellen und Nachweise

ORD-Eintrag
ord-031dbb932d9048a3867ea2e894df2e8e
Quelldatensatz
uspto-grants-1999_10
Patentnummer
US05962469

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