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Lithium Chloride → 4-(1-ethoxyvinyl)-7-methyl-2H-chromen-2-one

HRID 2422514
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HRID 2422514 반응식
FC(F)(F)S(O[C:7]1[C:16]2[C:11](=[CH:12][C:13]([CH3:17])=[CH:14][CH:15]=2)[O:10][C:9](=[O:18])[CH:8]=1)(=O)=O.C([Sn](CCCC)(CCCC)[C:26]([O:28][CH2:29][CH3:30])=[CH2:27])CCC.[Cl-].[Li+]>O1CCOCC1.C(OCC)(=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:29]([O:28][C:26]([C:7]1[C:16]2[C:11](=[CH:12][C:13]([CH3:17])=[CH:14][CH:15]=2)[O:10][C:9](=[O:18])[CH:8]=1)=[CH2:27])[CH3:30]
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참가 물질

7

반응물 3

HCID 433294Lithium ChlorideHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 233702387-Methyl-2-oxo-2H-chromen-4-YL trifluoromethanesulfonate

생성물 1

HCID 597748944-(1-ethoxyvinyl)-7-methyl-2H-chromen-2-one

시약·촉매·용매 3

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매
HCID 8857
Ethyl Acetate
용매
HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

To a solution of 7-methyl-2-oxo-2H-chromen-4-yl trifluoromethanesulfonate (prepared as described in U.S. Pat. No. 5,552,437) (2.5 g, 8.1 mmol) and tributyl(1-ethoxyvinyl)tin (2.88 mL, 8.5 mmol) in 1,4-dioxane (25 mL), lithium chloride (1.03 g, 24.3 mmol) was added. The reaction flask was then purged twice with nitrogen and tetrakis(triphenylphosphine) palladium(0) (468 mg, 0.405 mmol) was added. The reaction was then heated overnight at 100° C. After cooling, the reaction mixture was concentrated under reduced pressure and the crude residue obtained was diluted with ethyl acetate, washed with a saturated ammonium chloride aq. solution, water and brine, dried over MgSO4, filtered and concentrated. The crude residue obtained was purified by column chromatography (EtOAc/hexanes, 25:75 to 40:60) to afford the title compound. 1H NMR (400 MHz, acetone-d6): 7.76 (d, 1H), 7.22 (s, 1H), 7.19 (d, 1H), 6.35 (s, 1H), 4.64 (d, 1H), 4.61 (d, 1H), 4.04 (q, 2H), 2.47 (s, 3H), 1.40 (t, 3H).

후처리

  1. additionwas added
  2. temperatureAfter cooling
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. customthe crude residue obtained
  5. washwashed with a saturated ammonium chloride aq. solution, water and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude residue obtained
  10. customwas purified by column chromatography (EtOAc/hexanes, 25:75 to 40:60)

출처 및 근거

ORD 기록
ord-0c4c0dd4ea254113af1aa5f090f3cf78
출처 데이터셋
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07960409B2

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