Sodium Hydroxide → HCID 21110471, compound

HRID 1766935Notes

Reaction equation

HRID 1766935 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]#[N:12])[CH:9]=2)[CH2:4][O:3]1.[OH-:13].[Na+].[CH3:15][O:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Cl)=[CH:19][CH:18]=1.Cl[C:26]([O:28][CH2:29][CH:30]=[CH2:31])=[O:27]>O1CCCC1CO.CN(C1C=CN=CC=1)C.C(OCC)(=O)C.CCCCCC.ClCCl>[CH2:29]([O:28][C:26]([O:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]#[N:12])=[CH:9][C:10]=1[C:2]([O:1][CH2:21][C:20]1[CH:23]=[CH:24][C:17]([O:16][CH3:15])=[CH:18][CH:19]=1)=[O:13])=[O:27])[CH:30]=[CH2:31]

Participants

10

Reactant 4

HCID 14798Sodium HydroxideHCID 18052Allyl chloroformateHCID 699934-Methyloxybenzyl chlorideHCID 132895623-Oxo-1,3-dihydro-2-benzofuran-5-carbonitrile

Product 1

HCID 21110471HCID 21110471, compoundYield 46.9%

Reagents, catalysts & solvents 5

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 7360Tetrahydrofurfuryl alcoholSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

1-Oxo-1,3-dihydroisobenzofuran-6-carbonitrile (3.01 g, 18.9 mmol) obtained from Example 5-(2) was dissolved in a mixed solvent (200 ml) of tetrahydrofuran-methanol (3:1), and an aqueous solution of sodium hydroxide (1.004N; 17.4 ml, 17.4 mmol) was added thereto over a period of 10 minutes. The mixture was stirred at room temperature for 30 minutes, and the solvent was distilled off under reduced pressure. The resulting residue was dried using a vacuum pump. The obtained solid was dissolved in N,N-dimethylformamide (40 ml), and 4-methoxybenzyl chloride (2.96 g, 18.9 mmol) was added thereto. The mixture was heated at 70-80° C. for 1 hour. After cooling the mixture to 0° C., dichloromethane (40 ml) was added thereto, and 4-(N,N-dimethylamino)pyridine (5.78 g, 47.3 mmol) and allyl chloroformate (4.56 g, 37.9 mmol) were added thereto, then the mixture was stirred at the same temperature for 30 minutes. The mixture was diluted with ethyl acetate and then washed successively with water and an aqueous solution of sodium chloride. The resulting mixture was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to give an oily residue. The residue was subjected to chromatography on a silica gel (100 g) column (eluent; hexane:ethyl acetate=3:1) to afford the title compound (3.11 g, 43% yield) as a colorless oil.

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. customThe resulting residue was dried
  3. dissolutionThe obtained solid was dissolved in N,N-dimethylformamide (40 ml)
  4. temperatureThe mixture was heated at 70-80° C. for 1 hour
  5. temperatureAfter cooling the mixture to 0° C.
  6. stirringthe mixture was stirred at the same temperature for 30 minutes
  7. washwashed successively with water
  8. dry with materialThe resulting mixture was dried over anhydrous magnesium sulfate
  9. distillationthe solvent was distilled off under reduced pressure
  10. customto give an oily residue

Sources & evidence

ORD record
ord-18b7f0ef30864a6999f2889420e83ed1
Source dataset
uspto-grants-2007_06
Patent number
US07230023B2

Reaction notes

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