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

HRID 128512

反応式

HRID 128512 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 194336012-[3-Carboxypropyloxy]-dibenzofuran

試薬・触媒・溶媒 1

HCID 6569Methyl Ethyl Ketone溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-9f0b58938871469caa0115f86ab6fdaa
出典データセット
uspto-grants-1995_11
特許番号
US05464746

関連ノート

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