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

HRID 628836노트

반응식

HRID 628836 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 22242641Methanol--water (1/1)용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-eacd134d1bf742cd9958d01881426817
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09315467B2

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