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Dimethylformamide → 8-[(E)-2-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-vinyl]-6,6-dimethyl-6H-benzo[b]naphtho[2,3-d]furan-11-one

HRID 61919
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HRID 61919 반응식
CN(C=O)C.[CH3:6][C:7]1([CH3:33])[C:19]2[O:18][C:17]3[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=3[C:15]=2[C:14](=[O:24])[C:13]2[C:8]1=[CH:9][C:10](OS(C(F)(F)F)(=O)=O)=[CH:11][CH:12]=2.[CH3:34][C:35]1([CH3:42])[O:39][CH:38]([CH:40]=[CH2:41])[CH2:37][O:36]1.C([O-])(O)=O.[Na+]>C(OCC)(=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:34][C:35]1([CH3:42])[O:39][CH:38](/[CH:40]=[CH:41]/[C:10]2[CH:9]=[C:8]3[C:13](=[CH:12][CH:11]=2)[C:14](=[O:24])[C:15]2[C:16]4[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=4[O:18][C:19]=2[C:7]3([CH3:33])[CH3:6])[CH2:37][O:36]1
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참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 27350232,2-Dimethyl-4-vinyl-1,3-dioxolaneHCID 86663832Trifluoro-methanesulfonic acid 6,6-dimethyl-11-oxo-6,11-dihydro-benzo[b]naphtho[2,3-d]furan-8-yl ester

생성물 1

HCID 668341018-[(E)-2-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-vinyl]-6,6-dimethyl-6H-benzo[b]naphtho[2,3-d]furan-11-one수율 46%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

To the DMF solution (4 ml) of trifluoro-methanesulfonic acid 6,6-dimethyl-11-oxo-6,11-dihydro-benzo[b]naphtho[2,3-d]furan-8-yl ester (300 mg), 2,2-dimethyl-4-vinyl-[1,3]dioxolane (469 mg) and PdCl2(PPh3)2 (103 mg), sodium hydrocarbonate (184 mg) was added, and the mixture was stirred at 100° C. overnight under nitrogen atmosphere. The reaction mixture was diluted with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium bicarbonate and saturated brine, and then concentrated under reduced pressure. The resulting residues were purified by silica gel column (ethyl acetate/hexane) to obtain the title compound (130 mg, 46%).

후처리

  1. washThe organic layer was washed with saturated aqueous solution of sodium bicarbonate and saturated brine
  2. concentrationconcentrated under reduced pressure
  3. customThe resulting residues were purified by silica gel column (ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-ac3b347cde274544be77a0335828c70a
출처 데이터셋
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09440922B2

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