2-Nitropropane → HCID 21529568, compound

HRID 1657672Notes

Reaction equation

HRID 1657672 reaction equation
[Li].[N+:2]([CH:5]([CH3:7])[CH3:6])([O-:4])=[O:3].[N+]([C:11]1([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:14][CH2:13][CH2:12]1)([O-])=O>CN(C)P(N(C)C)(N(C)C)=O>[N+:2]([C:5]([C:11]1([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:14][CH2:13][CH2:12]1)([CH3:7])[CH3:6])([O-:4])=[O:3]

Participants

5

Reactant 3

HCID 3982-NitropropaneHCID 3028194LithiumHCID 21529567HCID 21529567, compound

Product 1

HCID 21529568HCID 21529568, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

The lithium salt of 2-nitropropane (9.9 g.) was dissolved in 200 ml. of hexamethylphosphoramide under nitrogen and ethyl 1-nitrocyclobutanecarboxylate was added. The mixture was stirred for three hours under fluorescent lighting. The mixture was then diluted with 400 ml. of water and extracted three times with 200 ml. portions of ether. The combined ether extracts were washed three times with water, dried over magnesium sulfate, and the ethyl 1-(α-nitroisopropyl)cyclobutanecarboxylate (70 percent yield) was recovered by distillation: b.p. (0.1 mm.), 62° C.

Workup

  1. additionThe mixture was then diluted with 400 ml
  2. extractionof water and extracted three times with 200 ml
  3. washThe combined ether extracts were washed three times with water
  4. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-5cb0278ffb074dd2852aec04e8cc921a
Source dataset
uspto-grants-1976_06
Patent number
US03962053

Reaction notes

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