Lithium hydroxide, monohydrate → 3-[4-(4-Isopropyl-phenyl)-pyridin-2-yl]-benzoic acid

HRID 628836ノート

反応式

HRID 628836 の反応式
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([C:16]3[CH:17]=[C:18]([CH:24]=[CH:25][CH:26]=3)[C:19]([O:21]CC)=[O:20])[CH:11]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].O.[OH-].[Li+]>CO.O>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([C:16]3[CH:17]=[C:18]([CH:24]=[CH:25][CH:26]=3)[C:19]([OH:21])=[O:20])[CH:11]=2)=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

参加物

4

反応物 2

HCID 168937Lithium hydroxide, monohydrateHCID 69232425Ethyl 3-[4-(4-isopropyl-phenyl)-pyridin-2-yl]-benzoate

生成物 1

HCID 116166883-[4-(4-Isopropyl-phenyl)-pyridin-2-yl]-benzoic acid収率 85.3%

試薬・触媒・溶媒 1

HCID 22242641Methanol--water (1/1)溶媒

実験手順

Part E. A solution of ethyl 3-[4-(4-isopropyl-phenyl)-pyridin-2-yl]-benzoate (116 mg, 0.34 mmol) in methanol-water (3 mL/1 mL) is treated with lithium hydroxide hydrate (41 mg, 1.7 mmol). The mixture is stirred at ambiemperature for 12 h., then partitioned between water and diethyl ether. The aqueous phase is neutralized to pH 7 with 3 N aq. HCl and extracted with ethyl acetate. The extract is washed with brine, dried over magnesium sulfate, filtered and evaporated to afford the title compound as a white powder (92 mg, 85%), m.p. 233-234° C. 1H NMR (300 MHz, methanol-d4): δ 8.66 (1H, s), 8.65 (1H, d, J=8 Hz), 8.25 (1H, d, J=8 Hz), 8.14-8.11 (2H, m), 7.78 (2H, d, J=9 Hz), 7.69-7.62 (2H, m), 7.42 (2H, d, J=9 hz), 3.00 (1H, heptet, J=7 Hz), 1.30 (6H, d, J=7 Hz). MS (ES+): m/e x. MS (ES−): m/e 319 (20), 318 (100).

後処理

  1. custompartitioned between water and diethyl ether
  2. extractionextracted with ethyl acetate
  3. washThe extract is washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

出典と根拠

ORDレコード
ord-eacd134d1bf742cd9958d01881426817
出典データセット
uspto-grants-2016_04
特許番号
US09315467B2

反応ノート

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