Hydrochloric Acid → 2-[(3-Chloro-3-methyl-2-nitrosobutoxy)methyl]-5-nitrofuran

HRID 1779752Notes

Reaction equation

HRID 1779752 reaction equation
[ClH:1].[N:2]([O:4]CCC(C)C)=O.[CH3:10][C:11]([CH3:24])=[CH:12][CH2:13][O:14][CH2:15][C:16]1[O:17][C:18]([N+:21]([O-:23])=[O:22])=[CH:19][CH:20]=1>>[Cl:1][C:11]([CH3:24])([CH3:10])[CH:12]([N:2]=[O:4])[CH2:13][O:14][CH2:15][C:16]1[O:17][C:18]([N+:21]([O-:23])=[O:22])=[CH:19][CH:20]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 8053Isoamyl NitriteHCID 189291392-[[(3-Methyl-2-butenyl)oxy]methyl]-5-nitrofuran

Product 1

HCID 189291312-[(3-Chloro-3-methyl-2-nitrosobutoxy)methyl]-5-nitrofuran

Conditions

Temperature
5 °C

Procedure

Concentrated HCl (2.5 mL) was added to a cooled (0°-5° C.) solution of isoamyl nitrite (14.0 g, 0.12 mol) and 2-[[(3-methyl-2-butenyl)oxy]methyl]-5-nitrofuran (4.0 g, 0.06 mol). The temperature was maintained below 5° C. during the addition and the reaction mixture was stirred at 5° C. for an additional 30 min. The product was filtered and washed with a cold (-20° C.) 1:1 mixture of ethanol and ether. The solid was further washed with ether to afford a light yellow solid. Yield 2.6 g (52%). mp 134°-135° C. 1H NMR (DMSO) 1.78 (ε 6H, CH3), 4.44 (s, 2H, HON=CCH2), 4.67 (s, 2H, CH2OAr ), 6.6 and 7.27 (d, 2H, ArH). MS: 277 (M+H)+

Workup

  1. temperatureThe temperature was maintained below 5° C. during the addition
  2. filtrationThe product was filtered
  3. washwashed with a cold (-20° C.) 1:1 mixture of ethanol and ether
  4. washThe solid was further washed with ether
  5. customto afford a light yellow solid

Sources & evidence

ORD record
ord-a34150d11450407b8fd5ddbeb0c1290c
Source dataset
uspto-grants-1997_05
Patent number
US05627286

Reaction notes

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