Potassium Carbonate → Benzyl 3-((8-(1,3-dioxolan-2-yl)octyl)oxy)-5-bromobenzoate

HRID 332658ノート

反応式

HRID 332658 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:15]=[C:16]([OH:18])[CH:17]=1)[C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6].Br[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH:28]1[O:32][CH2:31][CH2:30][O:29]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[O:29]1[CH2:30][CH2:31][O:32][CH:28]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][O:18][C:16]1[CH:15]=[C:4]([CH:3]=[C:2]([Br:1])[CH:17]=1)[C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 118323182-(8-Bromooctyl)-1,3-dioxolaneHCID 71093147Benzyl 3-bromo-5-hydroxybenzoate

生成物 1

HCID 71093165Benzyl 3-((8-(1,3-dioxolan-2-yl)octyl)oxy)-5-bromobenzoate収率 65%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

To a stirred solution of benzyl 3-bromo-5-hydroxybenzoate (2.85 g, 9.22 mmol) in dimethyl formamide (50 mL), was added 2-(8-bromooctyl)-1,3-dioxolane (2.44 g, 9.21 mmol) and potassium carbonate (1.91 g, 13.8 mmol), and the mixture stirred at 80° C. for 16 hours. The reaction mixture was cooled to room temperature, diluted with water and extracted with ethyl acetate (×3). The combined organic extracts were washed with brine, dried (magnesium sulphate), filtered, and concentrated under reduced pressure. The crude material was purified by silica gel chromatography eluting with 0-7% ethyl acetate in iso-hexane to afford the title compound (2.94 g, 65%).

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate (×3)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (magnesium sulphate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified by silica gel chromatography
  8. washeluting with 0-7% ethyl acetate in iso-hexane

出典と根拠

ORDレコード
ord-a8db384a0f6442fc9796af4e01bd80d0
出典データセット
uspto-grants-2014_11
特許番号
US08877774B2

反応ノート

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