Nitromethane → 6-(Nitromethyl)spiro[2.5]octan-6-ol

HRID 418480Notes

Reaction equation

HRID 418480 reaction equation
C[O-].[Na+].[CH2:4]1[C:6]2([CH2:11][CH2:10][C:9](=[O:12])[CH2:8][CH2:7]2)[CH2:5]1.[N+:13]([CH3:16])([O-:15])=[O:14]>CO>[N+:13]([CH2:16][C:9]1([OH:12])[CH2:10][CH2:11][C:6]2([CH2:5][CH2:4]2)[CH2:7][CH2:8]1)([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 10942334Sodium MethoxideHCID 19371017Spiro[2.5]octan-6-one

Product 1

HCID 666491866-(Nitromethyl)spiro[2.5]octan-6-olYield 55.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To 4M solution of sodium methoxide (14 mL) in methanol (10 mL) was added a solution of spiro[2.5]octan-6-one (4.6 g, 0.031 mol) and nitromethane (2.3 mL, 0.042 mol) in methanol (20 mL) at room temperature and stirred overnight. The reaction was quenched with acetic acid (4.5 mL) and water (50 mL) and the volatiles were removed under reduced pressure. The residue was extracted with dichloromethane (2×50 mL), and the combined extracts were dried, filtered and evaporated. The residue was purified by flash chromatography to afford the desired product (3.2 g, 52%).

Workup

  1. customThe reaction was quenched with acetic acid (4.5 mL) and water (50 mL)
  2. customthe volatiles were removed under reduced pressure
  3. extractionThe residue was extracted with dichloromethane (2×50 mL)
  4. customthe combined extracts were dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-a574beca46f5482d894c1154187e46c4
Source dataset
uspto-grants-2012_01
Patent number
US08093265B2

Reaction notes

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