Sodium Iodide → HCID 68514121, 화합물

HRID 1877118노트

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HRID 1877118 반응식
Cl[CH:2]([C:7]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[O:9][C:8]=1[CH3:18])[CH2:3][CH:4]([CH3:6])[CH3:5].[NH2:19][C:20]1[CH:29]=[CH:28][C:23]([C:24]([O:26]C)=[O:25])=[C:22]([O:30][CH3:31])[CH:21]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>CN(C)C(=O)C.O>[CH3:31][O:30][C:22]1[CH:21]=[C:20]([NH:19][CH:2]([C:7]2[CH:11]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[O:9][C:8]=2[CH3:18])[CH2:3][CH:4]([CH3:6])[CH3:5])[CH:29]=[CH:28][C:23]=1[C:24]([OH:26])=[O:25]

참가 물질

7

반응물 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 168705Methyl 4-amino-o-anisateHCID 68515497HCID 68515497, 화합물

생성물 1

HCID 68514121HCID 68514121, 화합물수율 46.2%

시약·촉매·용매 2

HCID 962Water용매HCID 31374Dimethylacetamide용매

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온도
80 °C

실험 절차

A mixture of 3-(1-chloro-3-methylbutyl)-2-methyl-5-phenylfuran (1.3 g), methyl 4-amino-2-methoxybenzoate (1.1 g), sodium carbonate (1.1 g) and sodium iodide (3.0 g) in N,N-dimethylacetamide (20 mL) was stirred overnight at 80° C. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was dissolved in methanol (5 mL) and tetrahydrofuran (5 mL), 2N lithium hydroxide (5 mL) was added, and the mixture was stirred at 70° C. for 6 hr. The reaction mixture was poured into water, and the mixture was acidified with 1N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (20% ethyl acetate/hexane to 50% ethyl acetate/hexane) to give the title compound (0.9 g, 46%) as an amorphous compound.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. dissolutionthe residue was dissolved in methanol (5 mL)
  6. additiontetrahydrofuran (5 mL), 2N lithium hydroxide (5 mL) was added
  7. stirringthe mixture was stirred at 70° C. for 6 hr
  8. additionThe reaction mixture was poured into water
  9. extractionextracted with ethyl acetate
  10. washThe organic layer was washed with saturated brine
  11. dry with materialdried over magnesium sulfate
  12. customThe solvent was evaporated under reduced pressure
  13. customthe residue was purified by silica gel chromatography (20% ethyl acetate/hexane to 50% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-9b1f542e695f4316a208fa4116b6ed7e
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08309580B2

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