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

HRID 1737313ノート

反応式

HRID 1737313 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-031dbb932d9048a3867ea2e894df2e8e
出典データセット
uspto-grants-1999_10
特許番号
US05962469

反応ノート

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