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Sodium Hydroxide → HCID 21110471, 화합물

HRID 1766935
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HRID 1766935 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

10

반응물 4

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

생성물 1

HCID 21110471HCID 21110471, 화합물수율 46.9%

시약·촉매·용매 5

HCID 14284
4-(Dimethylamino)pyridine
촉매
HCID 6344Dichloromethane용매
HCID 7360Tetrahydrofurfuryl alcohol용매
HCID 8058Hexane용매
HCID 8857Ethyl Acetate용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-18b7f0ef30864a6999f2889420e83ed1
출처 데이터셋
uspto-grants-2007_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07230023B2

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