Umbelliferone → 7-Hydroxychromanone

HRID 1464481

반응식

HRID 1464481 반응식
[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

참가 물질

5

반응물 2

HCID 5281426UmbelliferoneHCID 21226206Ethyl acetate hexane

생성물 1

HCID 2981307-Hydroxychromanone

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

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 vacuum to provide 7-hydroxydihydrocoumarin. Yield: 1.83 g; melting point 133°-135.5° C.;

후처리

  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 vacuum

출처 및 근거

ORD 기록
ord-cda8b0dbf11f44989e2f6f0ef078fbff
출처 데이터셋
uspto-grants-1994_04
특허 번호
US05304679

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