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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
ノート
印刷プレビュー

反応式

HRID 61919 の反応式
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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 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

生成物 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-one収率 46%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-ac3b347cde274544be77a0335828c70a
出典データセット
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09440922B2

反応ノート

読み込み中…

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