Hydrochloric Acid → Methyl 2-(2-chlorobenzylaminooxymethyl)-2-methylpropanoate

HRID 1722518Notes

Reaction equation

HRID 1722518 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[CH:4]=[N:5][O:6][CH2:7][C:8]([CH3:14])([CH3:13])[C:9]([O:11][CH3:12])=[O:10].Cl>C(O)C>[Cl:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[CH2:4][NH:5][O:6][CH2:7][C:8]([CH3:13])([CH3:14])[C:9]([O:11][CH3:12])=[O:10]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54572932Methyl 2-(2-chlorobenzylideneaminooxymethyl)-2-methylpropanoate

Product 1

HCID 20029228Methyl 2-(2-chlorobenzylaminooxymethyl)-2-methylpropanoateYield 28.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A mixture of methyl 2-(2-chlorobenzylideneaminooxymethyl)-2-methylpropanoate (10.0 grams, 0.04 mole) and borane-pyridine complex (10.4 mL; 0.12 mole) in absolute ethanol (30 mL) was cooled in an ice bath. A solution of anhydrous 6.5N hydrogen chloride in ethanol (60 mL) was then added slowly. Upon completion of addition, the reaction mixture was stirred at ambient temperature for four hours. The reaction mixture was concentrated under reduced pressure, and methylene chloride (50 mL) was added to the residue. Aqueous sodium carbonate was then added to adjust the pH to 6-7. The layers were separated, and the organic layer was dried (magnesium sulfate) and concentrated under reduced pressure to yield a mixture of a white solid and liquid. The liquid was decanted off and purified by chromatography through silica gel, eluting successively with hexane and 20:1 hexane:ethyl acetate. Appropriate fractions were combined and concentrated at reduced pressure to yield 3.1 grams of methyl 2-(2-chlorobenzylaminooxymethyl)-2-methylpropanoate as a colorless liquid.

Workup

  1. temperaturewas cooled in an ice bath
  2. additionUpon completion of addition
  3. concentrationThe reaction mixture was concentrated under reduced pressure, and methylene chloride (50 mL)
  4. additionwas added to the residue
  5. additionAqueous sodium carbonate was then added
  6. customThe layers were separated
  7. dry with materialthe organic layer was dried (magnesium sulfate)
  8. concentrationconcentrated under reduced pressure
  9. customto yield
  10. additiona mixture of a white solid and liquid
  11. customThe liquid was decanted off
  12. custompurified by chromatography through silica gel
  13. washeluting successively with hexane and 20:1 hexane
  14. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-c20c420274864f7495627179251c996a
Source dataset
uspto-grants-1989_08
Patent number
US04855480

Reaction notes

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