Ethylene Glycol → 5-(1,3-Dioxolan-2-yl)-1-benzofuran

HRID 2261105

반응식

HRID 2261105 반응식
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]=[O:11])=[CH:9][C:4]=2[CH:3]=[CH:2]1.[CH2:12](O)[CH2:13][OH:14].C(OC)(OC)OC.[Br-].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(O)=O.[Na+]>>[O:11]1[CH2:12][CH2:13][O:14][CH:10]1[C:8]1[CH:7]=[CH:6][C:5]2[O:1][CH:2]=[CH:3][C:4]=2[CH:9]=1

참가 물질

6

반응물 5

HCID 174Ethylene GlycolHCID 9005Trimethyl orthoformateHCID 516892Sodium BicarbonateHCID 27738751-Benzofuran-5-carbaldehydeHCID 23500184Tetra-n-butylammonium tribromide

생성물 1

HCID 552553255-(1,3-Dioxolan-2-yl)-1-benzofuran수율 36%

실험 절차

A mixture of benzofuran-5-carbaldehyde (150 mg, 1.03 mmol), ethylene glycol (230 ul, 4 eq), trimethyl orthoformate (123 ul, 1.1 eq) and tetrabutylammonium tribromide (49 mg, 0.1 eq) was stirred at room temperature for one night. Some starting material could be detected by TLC. However, the reaction mixture was poured into saturated NaHCO3 solution and the product was extracted with ethyl acetate. Combined organic layers were dried over anhydrous sodium sulfate, filtrated and concentrated to give a crude product, which was purified by flash chromatography using cyclohexane/ethyl acetate 20:0.75 as solvents. The title compounds was obtained in 36% yield (70 mg).

후처리

  1. extractionthe product was extracted with ethyl acetate
  2. dry with materialCombined organic layers were dried over anhydrous sodium sulfate
  3. filtrationfiltrated
  4. concentrationconcentrated
  5. customto give a crude product, which
  6. customwas purified by flash chromatography

출처 및 근거

ORD 기록
ord-eec14f946d8549d5928c933e3a13ea0a
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07846925B2

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