Nitromethane → 1-Cyclopropyl-2-nitroethan-1-ol

HRID 849161Notes

Reaction equation

HRID 849161 reaction equation
[CH2:1]1[CH:3]([CH:4]([OH:7])C#N)[CH2:2]1.[N+:8]([CH3:11])([O-:10])=[O:9].C(N(CC)CC)C>CO>[N+:8]([CH2:11][CH:4]([CH:3]1[CH2:1][CH2:2]1)[OH:7])([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 8471TriethylamineHCID 113893592-Cyclopropyl-2-hydroxyacetonitrile

Product 1

HCID 193693201-Cyclopropyl-2-nitroethan-1-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Example 319 A) To cyclopropyl carboxaldehyde in MeOH is added nitromethane and triethylamine. After stirring, the solvent is removed in vacuo and the residue is dissolved in CH2Cl2. The 2-nitro-1-cyclopropylethanol is isolated from the methylene chloride solution and added to a mixture of sodium acetate and acetic anhydride under N2After stirring, the mixture is diluted with water and extracted with EtOAc. The combined extracts are washed with brine, dried over MgSO4 and the solvent is removed in vacuo. The 2-nitroethenylcyclopropane is used without further purification.

Workup

  1. customthe solvent is removed in vacuo
  2. dissolutionthe residue is dissolved in CH2Cl2

Sources & evidence

ORD record
ord-42a4099cf986407cabd5be70692cf6c1
Source dataset
uspto-grants-2000_01
Patent number
US06011028

Reaction notes

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