Water → HCID 13557275, compound

HRID 1583486Notes

Reaction equation

HRID 1583486 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].C([O-])(=O)C.[Na+].Cl[CH2:19][CH2:20][C:21]([CH3:27])([CH3:26])[C:22]([O:24][CH3:25])=[O:23].O>CS(C)=O.C(OCC)(=O)C>[CH3:26][C:21]([CH3:27])([CH2:20][CH2:19][O:1][N:2]1[C:3](=[O:12])[C:4]2=[CH:11][CH:10]=[CH:9][CH:8]=[C:5]2[C:6]1=[O:7])[C:22]([O:24][CH3:25])=[O:23]

Participants

7

Reactant 4

HCID 962WaterHCID 10665N-HydroxyphthalimideHCID 517045Sodium AcetateHCID 13557274Methyl 4-chloro-2,2-dimethylbutanoate

Product 1

HCID 13557275HCID 13557275, compoundYield 60.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 83.2 grams (0.51 mole) of N-hydroxyphthalimide in 500 ml of dimethyl sulfoxide was added 41.8 grams (0.51 mole) of sodium acetate. Upon completion of addition the reaction mixture was stirred for one hour at ambient temperature. After this time 84.2 grams (0.51 mole) of methyl 4-chloro-2,2-dimethylbutanoate was added dropwise. The reaction mixture was then heated to 100° C. where it stirred for 16 hours. The reaction mixture was cooled and 300 ml of water and 1000 ml of ethyl acetate were added. The mixture was shaken and the organic layer separated. The organic layer was washed with three 200 ml portions of water. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residual oil. The oil was subjected to column chromatography on silica gel. Elution was accomplished with 1:3 ethyl acetate:heptane. The appropriate fractions were combined and concentrated under reduced pressure to a residual oil. The oil was dissolved in 500 ml of diethyl ether and washed with two 100 ml portions of aqueous 1N sodium hydroxide. The ether layer was concentrated under reduced pressure to give 90.3 grams of methyl 2,2-dimethyl-4-(phthalimidooxy)butanoate as an oil.

Workup

  1. additionUpon completion of addition the reaction mixture
  2. temperatureThe reaction mixture was then heated to 100° C. where it
  3. stirringstirred for 16 hours
  4. temperatureThe reaction mixture was cooled
  5. stirringThe mixture was shaken
  6. customthe organic layer separated
  7. washThe organic layer was washed with three 200 ml portions of water
  8. dry with materialThe organic layer was dried with magnesium sulfate
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated under reduced pressure to a residual oil
  11. washElution
  12. concentrationconcentrated under reduced pressure to a residual oil
  13. dissolutionThe oil was dissolved in 500 ml of diethyl ether
  14. washwashed with two 100 ml portions of aqueous 1N sodium hydroxide
  15. concentrationThe ether layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-278b114f8e6f4f3e92ef944b619b93d7
Source dataset
uspto-grants-1985_11
Patent number
US04552585

Reaction notes

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