Potassium Carbonate → HCID 69889373, compound

HRID 1581480Notes

Reaction equation

HRID 1581480 reaction equation
[CH3:1][C:2]1[O:3][C:4]([CH3:9])=[CH:5][C:6]=1[CH2:7]Br.C([O-])([O-])=O.[K+].[K+].[C:16]([O:20][C:21](=[O:24])[NH:22][NH2:23])([CH3:19])([CH3:18])[CH3:17]>CN(C=O)C.C(OCC)(=O)C>[C:16]([O:20][C:21]([NH:22][NH:23][CH2:7][C:6]1[CH:5]=[C:4]([CH3:9])[O:3][C:2]=1[CH3:1])=[O:24])([CH3:19])([CH3:18])[CH3:17]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 70091tert-Butyl carbazateHCID 22721975HCID 22721975, compound

Product 1

HCID 69889373HCID 69889373, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

To a stirred solution of 2,5-dimethyl-3-bromomethylfuran (5.95 mmol theor.) in DMF (30 mL) was added K2CO3 (1.64 g, 11.9 mmol) and tert-butylcarbazate (3.1 g, 23.8 mmol). The reaction was heated to 65° C. for 1 h. The reaction was cooled to room temperature, diluted with ethyl acetate and the layers separated. The organic layer was washed with saturated aqueous NH4Cl, water and brine and dried over Na2SO4. The mixture was filtered, concentrated and distilled on a Kuglerohr apparatus at 100° C. and 35 mTorr to remove the excess DMF and tert-butylcarbazate. This material was then purified using silica gel column chromatography (hexanes—4:1 hexanes:ethyl acetate as eluant) to afford the title compound as a dark yellow oil (670 mg, 2.79 mmol, 47% for the two steps). 1H NMR (300 MHz, DMSO-d6): δ 8.11 (br s, 1H); 5.91 (s, 1H); 4.38 (br s, 1H); 3.54 (s, 2H); 2.16 (s, 3H); 2.14 (s, 3H); 1.39 (s, 9H).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. customthe layers separated
  3. washThe organic layer was washed with saturated aqueous NH4Cl, water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationThe mixture was filtered
  6. concentrationconcentrated
  7. distillationdistilled on a Kuglerohr apparatus at 100° C.
  8. custom35 mTorr to remove the excess DMF and tert-butylcarbazate
  9. customThis material was then purified

Sources & evidence

ORD record
ord-e76d8b7108534f198f5275c63a5fafea
Source dataset
uspto-grants-2004_05
Patent number
US06730675B2

Reaction notes

Loading…