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 479972ノート

反応式

HRID 479972 の反応式
[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]

参加物

5

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 3283Diethyl Ether溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Benzyl ester 502 (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).

後処理

  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

出典と根拠

ORDレコード
ord-89267bb451f8418e98258eee77bf95bd
出典データセット
uspto-grants-2003_11
特許番号
US06649587B1

反応ノート

読み込み中…