3-(8-(1,3-Dioxolan-2-yl)octyloxy)benzaldehyde → (3-(8-(1,3-Dioxolan-2-yl)octyloxy)phenyl)(thiophen-2-yl)methanol

HRID 332653ノート

反応式

HRID 332653 の反応式
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=[O:19].[S:23]1[CH:27]=[CH:26][CH:25]=[C:24]1[Mg]Br>C1COCC1>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:16]=[C:17]([CH:18]([C:24]2[S:23][CH:27]=[CH:26][CH:25]=2)[OH:19])[CH:20]=[CH:21][CH:22]=1

参加物

4

反応物 2

HCID 866768973-(8-(1,3-Dioxolan-2-yl)octyloxy)benzaldehydeHCID 178418438HCID 178418438、化合物

生成物 1

HCID 71093201(3-(8-(1,3-Dioxolan-2-yl)octyloxy)phenyl)(thiophen-2-yl)methanol収率 88.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To a stirred solution of 3-(8-(1,3-dioxolan-2-yl)octyloxy)benzaldehyde (1.0 g, 3.25 mmol) in THF (30 mL) at −78° C. under an atmosphere of nitrogen, a solution of 2-thienylmagnesium bromide (1M in THF, 4.23 mL, 4.23 mmol) was added over 10 minutes. After stirring at −78° C. for 1 hour, the reaction was allowed to warm to RT and stirred for 16 hours. The reaction was quenched with saturated aqueous ammonium chloride solution and extracted with ethyl acetate (×3). The combined organic extracts were washed with brine, dried (magnesium sulfate), filtered, and concentrated under reduced pressure. The crude material was purified by silica gel chromatography eluting with 0-50% ethyl acetate in iso-hexane to afford the title compound (1.12 g, 87%).

後処理

  1. temperatureto warm to RT
  2. stirringstirred for 16 hours
  3. customThe reaction was quenched with saturated aqueous ammonium chloride solution
  4. extractionextracted with ethyl acetate (×3)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried (magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude material was purified by silica gel chromatography
  10. washeluting with 0-50% ethyl acetate in iso-hexane

出典と根拠

ORDレコード
ord-ed5b0dca12ec40b5b5c3acb9aca160ab
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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