Furan → HCID 23299778, compound

HRID 1952774Notes

Reaction equation

HRID 1952774 reaction equation
C([Li])CCC.[O:6]1[CH:10]=[CH:9][CH:8]=[CH:7]1.[CH:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[N:13][N:12]=1>O1CCCC1>[O:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[CH:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:11]=[N:12][NH:13]1

Participants

5

Reactant 3

HCID 8029FuranHCID 9207PhthalazineHCID 178418339Butyllithium

Product 1

HCID 23299778HCID 23299778, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

22.5 ml of an about 1.6M solution of butyllithium are slowly added dropwise at -78° C. to a solution of 2.46 g of furan in 30 ml of tetrahydrofuran. The mixture is stirred at -78° C. for 20 min., then at -20° C. for 2 hrs. The solution is again cooled to -78° C. and treated slowly with a solution of 4.68 g of phthalazine in 36 ml of tetrahydrofuran. The mixture is stirred at -78° C. for 2 hrs., then poured on to about 500 ml of ice-water and extracted 4 times with 150 ml of ethyl acetate each time. The organic phases are dried, concentrated and the residue is chromatographed immediately on 120 g of silica gel; eluent: hexane/ethyl acetate 3:7. 4.08 g of dark, impure 1-furan-2-yl-1,2-dihydrophthalazine are isolated.

Workup

  1. waitat -20° C. for 2 hrs
  2. temperatureThe solution is again cooled to -78° C.
  3. stirringThe mixture is stirred at -78° C. for 2 hrs
  4. extractionextracted 4 times with 150 ml of ethyl acetate each time
  5. customThe organic phases are dried
  6. concentrationconcentrated
  7. customthe residue is chromatographed immediately on 120 g of silica gel

Sources & evidence

ORD record
ord-25479a81212345f0bd5d9fbae1e88479
Source dataset
uspto-grants-2000_09
Patent number
US06114330

Reaction notes

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