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

HRID 1737313노트

반응식

HRID 1737313 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-031dbb932d9048a3867ea2e894df2e8e
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05962469

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