Acetic Acid → 1-(3-Benzyloxy-4-nitrobenzyl)-3,4-dihydro-1H-naphthalen-2-one

HRID 660565Notes

Reaction equation

HRID 660565 reaction equation
[Br-].[CH2:2]([O:9][C:10]1[CH:11]=[C:12]([CH:29]=[CH:30][C:31]=1[N+:32]([O-:34])=[O:33])[CH2:13][CH:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:17][CH2:16][C:15]1=[N+]1CCCC1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.O.C(Cl)(Cl)Cl.CC(O)=[O:42]>C(Cl)Cl>[CH2:2]([O:9][C:10]1[CH:11]=[C:12]([CH:29]=[CH:30][C:31]=1[N+:32]([O-:34])=[O:33])[CH2:13][CH:14]1[C:19]2[C:18](=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:17][CH2:16][C:15]1=[O:42])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 6212ChloroformHCID 688390331-[1-(3-Benzyloxy-4-nitrobenzyl)-3,4-dihydro-1H-naphthalen-2-ylidene]-pyrrolidinium Bromide

Product 1

HCID 688398621-(3-Benzyloxy-4-nitrobenzyl)-3,4-dihydro-1H-naphthalen-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-[1-(3-benzyloxy-4-nitrobenzyl)-3,4-dihydro-1H-naphthalen-2-ylidene]-pyrrolidinium bromide (700 mg, 1.59 mmol) in a mixed solvent of 10 mL H2O, 1 mL CHCl3 and 2 mL CH3COOH is stirred at RT for 3 h. The solution is diluted with CH2Cl2 and the organic layer is washed well with water, brine and dried over MgSO4. The solvent is removed under reduced pressure and the residue is purified by flash chromatography using a gradient of 33-50% EtOAc/hexane as eluent to give the title compound as a yellow liquid. NMR (CDCl3): 7.70-7.68 (d, J=8.34 Hz, 1H), 7.40-7.29 (m, 5H), 7.23-7.15 (m, 3H), 6.96-6.94 (dd, J=6.31 Hz, 1 H), 6.57-6.55 (m, 2H), 4.96 (s, 2H), 3.75-3.72 (t, J=6.07 Hz, 1H), 3.34-3.29 (q, J=6.82 Hz, 1H), 3.19-3.14 (q, J=5.30 Hz, 1H), 2.88-2.82 (m, 1H), 2.57-2.46 (m, 3H). (M−1)−=386.

Workup

  1. washthe organic layer is washed well with water, brine
  2. dry with materialdried over MgSO4
  3. customThe solvent is removed under reduced pressure
  4. customthe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-a4a8030012ba4c168d2ab2b89f97f568
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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