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

HRID 332653노트

반응식

HRID 332653 반응식
[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

참가 물질

4

반응물 2

HCID 866768973-(8-(1,3-Dioxolan-2-yl)octyloxy)benzaldehydeHCID 178418438HCID 178418438, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-ed5b0dca12ec40b5b5c3acb9aca160ab
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877774B2

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