Ethyl 2-hydroxyisobutyrate → Ethyl 2-methyl-2-{[(4-nitrophenoxy)carbonyl]oxy}propanoate

HRID 2047474Notes

Reaction equation

HRID 2047474 reaction equation
[OH:1][C:2]([CH3:9])([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:10](Cl)(=[O:21])[O:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1>C(#N)C.CN(C1C=CN=CC=1)C.O>[CH3:8][C:2]([O:1][C:10]([O:11][C:12]1[CH:13]=[CH:14][C:15]([N+:18]([O-:20])=[O:19])=[CH:16][CH:17]=1)=[O:21])([CH3:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

6

Reactant 2

HCID 6653Ethyl 2-hydroxyisobutyrateHCID 821294-Nitrophenyl chloroformate

Product 1

HCID 67232782Ethyl 2-methyl-2-{[(4-nitrophenoxy)carbonyl]oxy}propanoateYield 74%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of ethyl 2-hydroxy-2-methylpropanoate (1.2 g) and 4-nitrophenyl chlorocarbonate (1.2 g) in acetonitrile (20 mL) was added DMAP (0.77 g) at 0° C., and the mixture was stirred at room temperature for 3 days. The mixture was diluted with water, and extracted with ethyl acetate. The extract was washed with water and saturated brine, dried and concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (solvent gradient; 0→25% ethyl acetate/hexane) to give ethyl 2-methyl-2-{[(4-nitrophenoxy)carbonyl]oxy}propanoate (1.3 g, 74%) as a pale-yellow oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was separated
  6. custompurified by silica gel column chromatography (solvent gradient; 0→25% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-ffc2398177eb47e5a9845913ce9b6bb4
Source dataset
uspto-grants-2013_11
Patent number
US08592454B2

Reaction notes

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