Pyridine → (S)-2-(2-Bromo-6-methyl-4-nitrophenyl)-2-hydroxyethyl pivalate

HRID 1468707Notes

Reaction equation

HRID 1468707 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([CH3:11])[C:3]=1[C@H:12]([OH:15])[CH2:13][OH:14].N1C=CC=CC=1.[C:22](Cl)(=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24]>C(Cl)Cl>[C:22]([O:14][CH2:13][C@H:12]([C:3]1[C:4]([CH3:11])=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[Br:1])[OH:15])(=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 1049PyridineHCID 62493Pivaloyl chlorideHCID 70982486(S)-1-(2-Bromo-6-methyl-4-nitrophenyl)ethane-1,2-diol

Product 1

HCID 70982451(S)-2-(2-Bromo-6-methyl-4-nitrophenyl)-2-hydroxyethyl pivalate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of (S)-1-(2-bromo-6-methyl-4-nitrophenyl)ethane-1,2-diol (65D) (6.96 g, 25.22 mmol) in DCM (100 ml), was added pyridine (5 mL) at 0° C. To the solution was added pivaloyl chloride (PivCl) slowly at 0° C. The reaction mixture was stirred at 0° C. for 5 min, then raised to rt, stirred at rt for 5 h. The reaction mixture was washed by sat. NaHCO3, extracted by DCM, dry over MgSO4, filtered, purified by silica gel column, eluting by 0-40% EtOAc in Hexanes to give 9.13 g of 65E. The product taken on without full characterization.

Workup

  1. temperatureraised to rt
  2. stirringstirred at rt for 5 h
  3. washThe reaction mixture was washed by sat. NaHCO3
  4. extractionextracted by DCM
  5. dry with materialdry over MgSO4
  6. filtrationfiltered
  7. custompurified by silica gel column
  8. washeluting by 0-40% EtOAc in Hexanes

Sources & evidence

ORD record
ord-fffa4d50da1646eb8cb85f0e282f1d38
Source dataset
uspto-grants-2015_04
Patent number
US09006229B2

Reaction notes

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