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Triethylamine → Trans-3-Hydroxy-5-[2-(4-methoxyphenyl)ethenyl]phthalide

HRID 978651
ノート
印刷プレビュー

反応式

HRID 978651 の反応式
[OH:1][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9](Br)[CH:10]=2)[C:4](=[O:5])[O:3]1.[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[CH2:20])=[CH:17][CH:16]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.CS(C)=O>[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18](/[CH:19]=[CH:20]/[C:9]2[CH:10]=[C:11]3[C:6](=[CH:7][CH:8]=2)[C:4](=[O:5])[O:3][CH:2]3[OH:1])=[CH:17][CH:16]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 8471TriethylamineHCID 125074-MethoxystyreneHCID 80271Tri-o-tolylphosphineHCID 142348425-bromo-3-hydroxy-3H-isobenzofuran-1-one

生成物 1

HCID 13827310Trans-3-Hydroxy-5-[2-(4-methoxyphenyl)ethenyl]phthalide

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate
触媒
HCID 679Dimethyl Sulfoxide溶媒
HCID 962Water溶媒

実験手順

A mixture of 9.9 gm 3-hydroxy-5-bromophthalide, 5.8 gm p-methoxystyrene, 0.09 gm palladium acetate, 0.47 gm tri-(o-tolyl)-phosphine, 7 ml triethylamine and 35 ml dimethylsulfoxide were heated with stirring at 95° for 5 hours. The reaction mixture was cooled and added to 400 ml water. The product was extracted into ethyl acetate, which solution was washed with water and dried over magnesium sulfate. Removal of solvent left 8.0 gm yellow solid melting at 140°-148°.

後処理

  1. temperaturewere heated
  2. temperatureThe reaction mixture was cooled
  3. extractionThe product was extracted into ethyl acetate, which solution
  4. washwas washed with water
  5. dry with materialdried over magnesium sulfate
  6. customRemoval of solvent
  7. waitleft 8.0 gm yellow solid melting at 140°-148°

出典と根拠

ORDレコード
ord-dad1e319ca0b42ce852803f8944d4b4f
出典データセット
uspto-grants-1987_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04665181

反応ノート

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