Umbelliferone → 7-Hydroxychromanone

HRID 345746

反応式

HRID 345746 の反応式
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1.CCOC(C)=O.CCCCCC>C(O)C.[Pd]>[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1

参加物

5

反応物 2

HCID 5281426UmbelliferoneHCID 21226206Ethyl acetate hexane

生成物 1

HCID 2981307-Hydroxychromanone

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

A solution of 7-hydroxycoumarin (5.0 g, 0.031 mol; Aldrich Chemical Company) in absolute ethanol (200 mL) was hydrogenated under pressure in a Parr apparatus over 10% Pd/C (Catalyst; 500 mg, 50% water; Kodak Inc., Rochester, N.Y.) for 24 hours at 55° C. Thin layer chromatography (TLC; Silica gel: EtOAc/hexane: 1:1) showed completion of the reaction. The reaction mixture was then filtered over a bed of Celite (Rohm and Haas Co., Philadelphia, Pa.) and evaporated in vacuo to provide the crude product (4.5 g). A portion (2.5 g) of this material was recrystallized from toluene and dried under vaccuum to provide 7-hydroxydihydrocoumarin. Yield: 1.83 g; melting point 133°-135.5° C.;

後処理

  1. customcompletion of the reaction
  2. filtrationThe reaction mixture was then filtered over a bed of Celite (Rohm and Haas Co., Philadelphia, Pa.)
  3. customevaporated in vacuo
  4. customto provide the crude product (4.5 g)
  5. customA portion (2.5 g) of this material was recrystallized from toluene
  6. customdried under vaccuum

出典と根拠

ORDレコード
ord-9b32d0f1bd03423188c11a3d3e61c12a
出典データセット
uspto-grants-1991_10
特許番号
US05059438

関連ノート

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