Pyridine → Carbonic acid 2-methylallyl ester 4-nitrophenyl ester

HRID 2089635Notes

Reaction equation

HRID 2089635 reaction equation
[CH2:1]([OH:5])[C:2](=[CH2:4])[CH3:3].Cl[C:7]([O:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=1)=[O:8].N1C=CC=CC=1.[Cl-].[NH4+]>C1COCC1>[N+:16]([C:13]1[CH:12]=[CH:11][C:10]([O:9][C:7](=[O:8])[O:5][CH2:1][C:2]([CH3:3])=[CH2:4])=[CH:15][CH:14]=1)([O-:18])=[O:17]

Participants

6

Reactant 4

HCID 1049PyridineHCID 10557Methallyl alcoholHCID 25517Ammonium ChlorideHCID 821294-Nitrophenyl chloroformate

Product 1

HCID 67469869Carbonic acid 2-methylallyl ester 4-nitrophenyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methallyl alcohol [CAS No. 513-42-8] (5 g) and 4-nitrophenyl chloroformate [CAS No. 7693-46-1] (12.6 g) were dissolved in THF (70 mL), and pyridine (6.69 mL) was added to the resulting mixture under ice-cooling, after which the resulting mixture was stirred overnight at room temperature. To the reaction mixture, ice and saturated aqueous ammonium chloride solution were added, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The resulting mixture was filtered, and the filtrate obtained was concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography (mixed solvent of heptane-ethyl acetate) to obtain the captioned compound (10.5 g).

Workup

  1. temperaturecooling
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe resulting mixture was filtered
  6. customthe filtrate obtained
  7. concentrationwas concentrated under reduced pressure
  8. customThe residue obtained
  9. customwas purified by silica gel column chromatography (mixed solvent of heptane-ethyl acetate)

Sources & evidence

ORD record
ord-b0bc7230f5da40cc88c91493b35446c3
Source dataset
uspto-grants-2013_05
Patent number
US08436009B2

Reaction notes

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