18-Crown-6 → 2-Nitro 1-[di-(t-butyl)methoxy]propane

HRID 1906120Notes

Reaction equation

HRID 1906120 reaction equation
[C:1]([CH:5]([C:7]([CH3:10])([CH3:9])[CH3:8])[OH:6])([CH3:4])([CH3:3])[CH3:2].C([Li])(CC)C.C1OCCOCCOCCOCCOCCOC1.[N+:34]([C:37]([CH3:39])=[CH2:38])([O-:36])=[O:35]>C(#N)C.O1CCCC1>[N+:34]([CH:37]([CH3:39])[CH2:38][O:6][CH:5]([C:7]([CH3:10])([CH3:9])[CH3:8])[C:1]([CH3:4])([CH3:3])[CH3:2])([O-:36])=[O:35]

Participants

7

Reactant 4

HCID 2855718-Crown-6HCID 784862-Nitro-1-propeneHCID 1397902,2,4,4-Tetramethylpentan-3-olHCID 178418400CID 53628100

Product 1

HCID 139072452-Nitro 1-[di-(t-butyl)methoxy]propane

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Di-t-butylmethanol is added to a dry flask under argon at 0° C. Dry tetrahydrofuran is added with a syringe. Sec-Butyl lithium (1.5M in Hexanes) is added quickly in one portion and the contents of the flask are stirred for one hour at room temperature. A 10 mM solution of 18-crown-6-ether in acetonitrile is added with a syringe and the flask cooled to 0° C. A tetrahydrofuran solution of 2-nitropropene is added with vigorous stirring over a 10 minute period. After completion of the reaction as judged by thin layer chromatography, it is quenched with saturated ammonium chloride and extracted with ethyl acetate. The organic layer is dried over MgSO4 and evaporated to yield 2-nitro 1-[di-(t-butyl)methoxy]propane.

Workup

  1. temperaturethe flask cooled to 0° C
  2. stirringwith vigorous stirring over a 10 minute period
  3. customAfter completion of the reaction
  4. customis quenched with saturated ammonium chloride
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic layer is dried over MgSO4
  7. customevaporated

Sources & evidence

ORD record
ord-9c239f608e2445dab4bc3d523d57bfc9
Source dataset
uspto-grants-1987_03
Patent number
US04650688

Reaction notes

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