Tetrahydrofuran → 1-Furan-2-ylmethyl-6-methoxy-4-phenyl-phthalazine

HRID 2297494Notes

Reaction equation

HRID 2297494 reaction equation
C1COCC1.[C:6]1([Li])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl[C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([O:24][CH3:25])[CH:22]=2)[C:17]([CH2:26][C:27]2[O:28][CH:29]=[CH:30][CH:31]=2)=[N:16][N:15]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(OCC)(=O)C.[Cl-].[Cl-].[Zn+2].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[O:28]1[CH:29]=[CH:30][CH:31]=[C:27]1[CH2:26][C:17]1[C:18]2[C:23](=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)[C:14]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[N:15][N:16]=1

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 121090664-Chloro-1-furan-2-ylmethyl-6-methoxy-phthalazineHCID 178506676HCID 178506676, compound

Product 1

HCID 121090671-Furan-2-ylmethyl-6-methoxy-4-phenyl-phthalazineYield 34.7%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 3007855ZincchlorideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution under N2 of ZnCl2 in THF 0.5M (18.35 ml, 9.18 mmoles) was dropwise added under stirring at 0° C. with 2M phenyl lithium (4.37 ml, 8.74 mmoles). The mixture was left at room temperature for 1 hour, then sequentially added with 4-chloro-1-furan-2-ylmethyl-6-methoxy-phthalazine (1.2 g, 4.37 mmoles), prepared as described in example 127, palladium acetate (49 mg, 0.218 mmole) and triphenylphosphine (114.4 mg, 4.36 mmoles). The mixture was refluxed for 45 minutes, then diluted with ethyl acetate and washed with water. The organic phase was anhydrified over Na2SO4 and dried. The residue was flash chromatographed (eluent: petrolatum/ethyl acetate 1:1). The resultant oil was crystallised from ethyl ether (15 ml) to give 480 mg of the title compound (yield: 34%). m.p.: 128-129° C.

Workup

  1. customprepared
  2. temperatureThe mixture was refluxed for 45 minutes
  3. washwashed with water
  4. customdried
  5. customchromatographed (eluent: petrolatum/ethyl acetate 1:1)
  6. customThe resultant oil was crystallised from ethyl ether (15 ml)

Sources & evidence

ORD record
ord-13f227eb53f04a0898ea3c73d2772fc3
Source dataset
uspto-grants-2002_12
Patent number
US06492360B1

Reaction notes

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