4-Hydroxybenzaldehyde → HCID 86676461、化合物

HRID 1472756ノート

反応式

HRID 1472756 の反応式
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]1[O:11][CH2:10][CH2:9][O:8]1.[OH:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[O:8]1[CH2:9][CH2:10][O:11][CH:7]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][O:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=1

参加物

6

反応物 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 5520822-(5-bromopentyl)-1,3-dioxolane

生成物 1

HCID 86676461HCID 86676461、化合物収率 37.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

To a stirred solution of 2-(5-bromopentyl)-1,3-dioxolane (4.38 g, 19.6 mmol) in dimethyl formamide (30 mL) was added 4-hydroxybenzaldehyde (3.00 g, 24.4 mmol) and potassium carbonate (4.52 g, 32.8 mmol). The reaction mixture was stirred at 50° C. for 16 hours. The reaction mixture was diluted with water and extracted with ethyl acetate (×3). The combined organic extracts were washed with saturated aqueous sodium hydrogen carbonate solution and brine, dried (sodium sulfate), filtered and concentrated under reduced pressure to afford an oil. The crude material was purified by silica gel column chromatography eluting with 0-100% ethyl acetate in iso-hexane to afford the title compound (1.92 g, 36%).

後処理

  1. extractionextracted with ethyl acetate (×3)
  2. washThe combined organic extracts were washed with saturated aqueous sodium hydrogen carbonate solution and brine
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto afford an oil
  7. customThe crude material was purified by silica gel column chromatography
  8. washeluting with 0-100% ethyl acetate in iso-hexane

出典と根拠

ORDレコード
ord-13b77e9088c2420fbd97e835a3e4e17d
出典データセット
uspto-grants-2015_04
特許番号
US09012644B2

反応ノート

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