Furan → HCID 13243429, compound

HRID 2295861Notes

Reaction equation

HRID 2295861 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8](N)[C:7]=1[CH3:13])(=[O:3])[CH3:2].[O:14]1[CH:18]=[CH:17][CH:16]=[CH:15]1.N(OC(C)(C)C)=O>CCCCCCC>[C:1]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:15]2[O:14][CH:18]=[CH:17][CH:16]=2)[C:7]=1[CH3:13])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8029FuranHCID 10906Tert-Butyl nitriteHCID 132459393-Amino-2-methylphenylmethyl acetate

Product 1

HCID 13243429HCID 13243429, compoundYield 32.4%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

A stirred solution of 10.0 g (0.056 mol) of 3-amino-2-methylphenylmethyl acetate and 37.4 g (0.055 mol) of furan was heated to reflux, and 8.6 g (0.084 mol) of tert-butyl nitrite was added dropwise during 30 minutes. Upon complete addition, the reaction mixture was heated under reflux an additional 1.5 hours, then cooled, and 300 mL of heptane was added. The solution was filtered through 50 g of silica gel. The silica gel was washed with 400 mL of pentane. The wash and filtrate were combined and concentrated under reduced pressure to give a residual oil which was subjected to column chromatography on silica gel, eluting with toluene. The appropriate fractions were combined and concentrated under reduced pressure to give a residual oil. The oil was subjected to distillation under reduced pressure using a Kugelrohr distilling system to give 4.1 g of 3-(2-furanyl)-2-methylphenylmethyl acetate, b.p. 94±2° C./0.05 mm.

Workup

  1. temperatureto reflux
  2. additionUpon complete addition
  3. temperaturethe reaction mixture was heated
  4. temperatureunder reflux an additional 1.5 hours
  5. temperaturecooled
  6. filtrationThe solution was filtered through 50 g of silica gel
  7. washThe silica gel was washed with 400 mL of pentane
  8. washThe wash
  9. concentrationconcentrated under reduced pressure
  10. customto give a residual oil which
  11. washeluting with toluene
  12. concentrationconcentrated under reduced pressure
  13. customto give a residual oil
  14. distillationThe oil was subjected to distillation under reduced pressure
  15. distillationdistilling system

Sources & evidence

ORD record
ord-0ec23a7a2d774a4fac9947d5a4ebd312
Source dataset
uspto-grants-1984_01
Patent number
US04426524

Reaction notes

Loading…