6-Nitro-1a,2,3,7b-tetrahydronaphtho[1,2-b]oxirene → 7-Nitro-2-tetralone

HRID 1157625Notes

Reaction equation

HRID 1157625 reaction equation
[N+:1]([C:4]1[CH:14]=[C:13]2[C:7]([CH2:8][CH2:9][CH:10]3[O:12][CH:11]32)=[CH:6][CH:5]=1)([O-:3])=[O:2]>C1C=CC=CC=1.[I-].[Zn+2].[I-]>[N+:1]([C:4]1[CH:14]=[C:13]2[C:7]([CH2:8][CH2:9][C:10](=[O:12])[CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 1

HCID 145667296-Nitro-1a,2,3,7b-tetrahydronaphtho[1,2-b]oxirene

Product 1

HCID 113214437-Nitro-2-tetraloneYield 58%

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 241BenzeneSolvent

Procedure

6-Nitro-1a,2,3,7b-tetrahydronaphtho[1,2-b]oxirene (1.3 g, 6.8 mmol) was combined with anhydrous zinc iodide powder (1.0 g, 3.1 mmol) in benzene and stirred at rt under nitrogen in a dark vessel for 15 h. The reaction mixture was filtered and the filtrate concentrated under vacuum. The crude residue was purified by silica gel flash column chromatography (10-50% EtOAc/hexanes) to yield 750 mg (58%) of the desired ketone as a yellow powder. 1H NMR (400 MHz, DMSO-d6) δ 8.09 (d, J=2.1 Hz, 1H), 8.06 (dd, J=8.2, 2.4 Hz, 1H), 7.55 (d, J=8.3 Hz, 1H), 3.75 (s, 2H), 3.15 (t, J=6.7 Hz, 2H), 2.50-2.43 (m, 4H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentrated under vacuum
  3. customThe crude residue was purified by silica gel flash column chromatography (10-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-913845a0ff5845709c6f99fba4e047ac
Source dataset
uspto-grants-2010_10
Patent number
US07807673B2

Reaction notes

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