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Ethylene Glycol → 6-Bromospiro[2H-1-benzopyran-3(4H),2'-[1,3]dioxolane]

HRID 1408432
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인쇄 미리보기

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HRID 1408432 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][C:8](=[O:11])[CH2:7][C:6]=2[CH:12]=1.[CH2:13](O)[CH2:14][OH:15].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][C:8]3([O:15][CH2:14][CH2:13][O:11]3)[CH2:7][C:6]=2[CH:12]=1
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참가 물질

5

반응물 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 584666226-bromo-3,4-dihydro-2H-1-benzopyran-3-one

생성물 1

HCID 671512246-Bromospiro[2H-1-benzopyran-3(4H),2'-[1,3]dioxolane]수율 94.7%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
100 °C

실험 절차

To a solution of 6-bromo-2H-1-benzopyran-3(4H)-one (300 mg, 1.13 mmol) in toluene (2 mL) was added ethyleneglycol (163 mg 2.64 mmol) and para-toluenesulfonic acid (27 mg, 0.13 mmol). The reaction mixture was heated at 100° C. for 6 hrs. The reaction mixture was cooled and the solvent concentrated. The resultant residue was partitioned between ethyl acetate and water. The organic phase was washed with water, brine, dried over Na2SO4 and concentrated under vacuum to give the title compound (290 mg, 79% yield) as a solid.

후처리

  1. temperatureThe reaction mixture was cooled
  2. concentrationthe solvent concentrated
  3. customThe resultant residue was partitioned between ethyl acetate and water
  4. washThe organic phase was washed with water, brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-c80036f10e2745eda52e07e53243a9f5
출처 데이터셋
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08921360B2

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