Benzyl 5-[(1,2-dihydro-1,2-dioxonaphth-4-yl)oxy]valerate → 5-[(1,2-Dioxo-1,2-dihydronaphth-4-yl)oxy]valeric Acid

HRID 852813노트

반응식

HRID 852813 반응식
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19]CC2C=CC=CC=2)=[O:18])=[CH:4][C:3]1=[O:27]>C(OCC)(=O)C.CCOCC.[Pd]>[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:4][C:3]1=[O:27]

참가 물질

5

반응물 1

HCID 22647819Benzyl 5-[(1,2-dihydro-1,2-dioxonaphth-4-yl)oxy]valerate

생성물 1

HCID 226478225-[(1,2-Dioxo-1,2-dihydronaphth-4-yl)oxy]valeric Acid수율 37%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 3283Diethyl Ether용매HCID 8857Ethyl Acetate용매

실험 절차

Benzyl ester 2 (1.90 g, 5.22 mmol) was hydrogenated at 30 psi with Pd (400 mg) in ethyl acetate (120 mL) for 6 h. The catalyst was removed by filtration through celite, the solvent was evaporated in vacuo and the residue was oxidized with Ag2O (1.45 g, 6.25 mmol) in Et2O by stirring for 10 h. Following filtration and evaporation of the solvent the product was crystallized from benzene to afford 0.53 g of pure material. The mother liquor was purified by flash chromatography (CH2Cl2/MeOH 15:1), the product dissolved in CH2Cl2, extracted with aqueous NaHCO3 solution, acidified to pH 1 with 3% HCl and extracted back with CH2Cl2 to give additional 0.25 g of pure material (total yield 55%), mp 134-136° C.; 1H NMR (CDCl3) 8.12 (d, J=7.0 Hz, 1H), 7.87 (d, J=7.6 Hz, 1H), 7.70 (t, J=7.5 Hz, 1H), 7.59 (t, J=7.4 Hz, 1H), 7.27 (s, 1H), 4.18 (t, J=5.9 Hz, 2H), 2.51 (t, J=7.0 Hz, 2H), 1.75-2.15 (m, 4H).

후처리

  1. customThe catalyst was removed by filtration through celite
  2. customthe solvent was evaporated in vacuo
  3. filtrationfiltration and evaporation of the solvent the product
  4. customwas crystallized from benzene

출처 및 근거

ORD 기록
ord-76a0c7ab960f47d6b26f7cd5688ed690
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07253207B2

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