N,N,N',N'-Tetramethylethylenediamine → HCID 516434, compound

HRID 2215665Notes

Reaction equation

HRID 2215665 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3]C.[CH3:6]CCCCC.CN(C)CCN(C)C.[C:20]([C:23]1[O:24][CH:25]=[CH:26][CH:27]=1)(=O)[CH3:21].C([C:30]12[C:40](C(C)C)=[CH:39][CH:38]=[CH:37][CH:36]1[NH:35][C:34](=O)[O:33][C:31]2=O)C>C1COCC1.[Cl-].[NH4+]>[CH2:34]([N:35]1[C:36]2[C:30](=[CH:40][C:39]([CH:2]([CH3:3])[CH3:1])=[CH:38][CH:37]=2)[C:31](=[O:33])[CH:21]=[C:20]1[C:23]1[O:24][CH:25]=[CH:26][CH:27]=1)[CH3:6]

Participants

8

Reactant 5

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 8058HexaneHCID 145052-AcetylfuranHCID 86590748HCID 86590748, compoundHCID 178418339Butyllithium

Product 1

HCID 516434HCID 516434, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 25517Ammonium ChlorideSolvent

Procedure

To a 1.6M solution of n-butyl lithium in hexane (1,38 mL, 2,2 mmol) was added tetramethylethylenediamine (0.3 mL, 2,2 mmol) under argon atmosphere at room temperature with stirring. Then 2-acetylfuran (242 mg, 2,2 mmol) in anhydrous THF was added dropwise to the mixture under ice cooling followed by stirring for 1 hour. To this mixture was added 1-ethyl-6-isopropylisatoic anhydride (250 mg, 1.1 mmol) in anhydrous THF. After stirring at room temperature overnight, the reaction mixture was diluted with saturated aqueous solution of ammonium chloride. The resulting organic layer was separated and concentrated under reduced pressure. The residue was dissolved in ethyl acetate and then washed with saturated sodium chloride solution followed by drying with sodium sulfate. After removing ethyl acetate by evaporation in vacuo, the residue was subjected to preparative TLC(n-hexane:ethyl acetate=2:1) to separate the title compound followed by crystallization from diethyl ether. 1H-NMR (CDCl3) δ 1.33 (6H, d, CH(CH3)2), 1.55 (3H, t, CH2CH3), 3.08 (1H,septet,CH), 4.17 (2H, q, NCH2), 6.48 (1H, s, H-3), 6.56-6.58 (1H, m, furan H-4′), 6.76 (1H, dd, furan H-5′), 7.54 (1H, d, H-8), 7.59 (1H, dd, H-7), 7.63 (1H, dd, furan H-3′), 8.34 (1H, d, H-5)

Workup

  1. stirringby stirring for 1 hour
  2. stirringAfter stirring at room temperature overnight
  3. customThe resulting organic layer was separated
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed with saturated sodium chloride solution
  7. dry with materialby drying with sodium sulfate
  8. customAfter removing ethyl acetate
  9. customby evaporation in vacuo
  10. customto separate the title compound
  11. customfollowed by crystallization from diethyl ether

Sources & evidence

ORD record
ord-9bafa892d4774f34b1cd7ce134e33de5
Source dataset
uspto-grants-2006_09
Patent number
US07109338B2

Reaction notes

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