Ammonium nitrate → HCID 86751439, compound

HRID 1490130Notes

Reaction equation

HRID 1490130 reaction equation
S1CCCS[CH:2]1[CH:7]1[CH2:11][CH2:10][CH:9]([O:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH2:8]1.[N+]([O-])([O-])=[O:21].[NH4+]>C(#N)C.O>[F:19][C:16]1[CH:17]=[CH:18][C:13]([O:12][C@@H:9]2[CH2:10][CH2:11][C@H:7]([CH:2]=[O:21])[CH2:8]2)=[CH:14][CH:15]=1.[F:19][C:16]1[CH:17]=[CH:18][C:13]([O:12][C@H:9]2[CH2:10][CH2:11][C@H:7]([CH:2]=[O:21])[CH2:8]2)=[CH:14][CH:15]=1

Participants

6

Reactant 2

HCID 22985Ammonium nitrateHCID 21480854HCID 21480854, compound

Product 2

HCID 86751438HCID 86751438, compoundYield 20%HCID 86751439HCID 86751439, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 1-(1,3-dithian-2-yl)-3-(4-fluorophenoxy)cyclopentane (10.0 g, 33.5 mmol) in 75% aqueous acetonitrile (300 ml) was added eerie ammonium nitrate (J. Chem Soc., Chem. Commun., 1977, 680) (74.0 g, 135 mmol) at room temperature. The reaction mixture was stirred for 0.5 h at the same temperature, diluted with water (500 ml) and then extracted with ether (500 ml). The ether phase was washed with brine (300 ml), dried (MgSO4) and concentrated in vacuo. Purification by flash column chromatography {SiO2, 250 g; hexane/ethyl acetate (10:1)} gave 1.28 g (20%) of cis-3-(4-fluorophenoxy)cyclopentanecarbaldehyde (Rf=0.2), 2.35 g (37%) of trans-3-(4-fluorophenoxy)cyclopentanecarbaldehyde (Rf=0.25) and 1.01 g (17%) of cis/trans mixture, respectively, as colorless oils: cis-3-(4-fluorophenoxy)cyclopentanecarbaldehyde; 1H NMR δ9.66 (s, 1H), 7.06-6.90 (m, 2H), 6.86-6.75 (m, 2H), 4.87-4.73 (m, 1H), 2.91-2.73 (m, 1H), 2.40-1.80 (m, 6H): trans-3-(4-fluorophenoxy)cyclopentanecarbaldehyde; 1H NMR δ9.71 (s, 1H), 7.05-6.91 (m, 2H), 6.90-6.75 (m, 2H), 4.87-4.72 (m, 1H), 3.25-3.01 (m, 1H), 2.32-1.79 (m, 6H).

Workup

  1. extractionextracted with ether (500 ml)
  2. washThe ether phase was washed with brine (300 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customPurification by flash column chromatography {SiO2, 250 g

Sources & evidence

ORD record
ord-be531511a87a49ce8bf0661d231f513b
Source dataset
uspto-grants-1997_10
Patent number
US05681858

Reaction notes

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