Ethyl Acetate → (S)-2-(2-Bromo-6-methyl-4-nitrophenyl)-2-tert-butoxyethyl pivalate

HRID 1468708Notes

Reaction equation

HRID 1468708 reaction equation
[C:1]([O:7][CH2:8][C@H:9]([C:11]1[C:16]([CH3:17])=[CH:15][C:14]([N+:18]([O-:20])=[O:19])=[CH:13][C:12]=1[Br:21])[OH:10])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].CCOC(C)=O.C(O[C:32]([CH3:35])([CH3:34])[CH3:33])(=O)C>>[C:1]([O:7][CH2:8][C@H:9]([C:11]1[C:16]([CH3:17])=[CH:15][C:14]([N+:18]([O-:20])=[O:19])=[CH:13][C:12]=1[Br:21])[O:10][C:32]([CH3:35])([CH3:34])[CH3:33])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

4

Reactant 3

HCID 8857Ethyl AcetateHCID 10908tert-Butyl acetateHCID 70982451(S)-2-(2-Bromo-6-methyl-4-nitrophenyl)-2-hydroxyethyl pivalate

Product 1

HCID 70981268(S)-2-(2-Bromo-6-methyl-4-nitrophenyl)-2-tert-butoxyethyl pivalateYield 85%

Conditions

Temperature
0 °C

Procedure

To a solution of (S)-2-(2-bromo-6-methyl-4-nitrophenyl)-2-hydroxyethyl pivalate (65E) in t-butyl acetate at 0° C., was added HClO4 (perchloric acid) (5.45 ml) slowly, stirred at 0° C. for 5 min, then the reaction mixture was warmed up to rt and stirred for 3 hs. The mixture was diluted by EtOAc, washed by sat. NaHCO3, extracted by EtOAc, dry over MgSO4, filtered, concentrated down and purified by silica gel column, eluting by 0-100% EtOAc in Hexanes to give 65F (9 g, 85%).

Workup

  1. temperaturethe reaction mixture was warmed up to rt
  2. stirringstirred for 3 hs
  3. washwashed by sat. NaHCO3
  4. extractionextracted by EtOAc
  5. dry with materialdry over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated down
  8. custompurified by silica gel column
  9. washeluting by 0-100% EtOAc in Hexanes

Sources & evidence

ORD record
ord-00992e606cba4fe9aa9e23830205990f
Source dataset
uspto-grants-2015_04
Patent number
US09006229B2

Reaction notes

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