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

HRID 1737313Notes

Reaction equation

HRID 1737313 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-031dbb932d9048a3867ea2e894df2e8e
Source dataset
uspto-grants-1999_10
Patent number
US05962469

Reaction notes

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