Sodium Iodide → 2-[3-Carboxypropyloxy]-dibenzofuran

HRID 128512

반응식

HRID 128512 반응식
[OH:1][C:2]1[CH:14]=[CH:13][C:5]2[O:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:4]=2[CH:3]=1.[CH2:15]([C:17](Br)(CC)[C:18]([O-:20])=[O:19])[CH3:16].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CC(=O)CC>[C:18]([CH2:17][CH2:15][CH2:16][O:1][C:2]1[CH:14]=[CH:13][C:5]2[O:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:4]=2[CH:3]=1)([OH:20])=[O:19]

참가 물질

6

반응물 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 665872-DibenzofuranolHCID 21584491Ethylbromobutyrate

생성물 1

HCID 194336012-[3-Carboxypropyloxy]-dibenzofuran

시약·촉매·용매 1

HCID 6569Methyl Ethyl Ketone용매

실험 절차

2-Hydroxydibenzofuran (0.5 gm, 2.7 mmol), ethylbromobutyrate (0.78 mL, 5.4 mmol), potassium carbonate (1.1 gm, 8.1 mmol), and sodium iodide (10 mg) were combined in 2-butanone (15 mL). The reaction was refluxed until complete, then the reaction filtered and the solvent removed under reduced pressure. The residue was taken up in 6M aqueous KOH/methanol, 1:1. After the hydrolysis was complete the reaction was acidified to pH 3 and the product extracted with ethyl acetate. The residue was purified by column chromatography (silica gel, ethyl acetate/hexanes/acetic acid, 10:30:60:0.5). The yield was 0.52 gm of product. Mass spectrum: DCI/NH3, (m+H)+ @ m/z 271, (m+NH4)+ @ m/z 288, (m+NH4 ·NH3)+ @ m/z 305.

후처리

  1. temperatureThe reaction was refluxed until complete, then the reaction
  2. filtrationfiltered
  3. customthe solvent removed under reduced pressure
  4. extractionthe product extracted with ethyl acetate
  5. customThe residue was purified by column chromatography (silica gel, ethyl acetate/hexanes/acetic acid, 10:30:60:0.5)

출처 및 근거

ORD 기록
ord-9f0b58938871469caa0115f86ab6fdaa
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05464746

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