Lithium hydroxide, monohydrate → 2'-Ethyl-2-(methoxymethyl)-[1,1'-biphenyl]-4-carboxylic acid

HRID 2410482노트

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HRID 2410482 반응식
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15]([O:17]C)=[O:16])=[CH:11][C:10]=1[CH2:19][O:20][CH3:21])[CH3:2].O.[OH-].[Li+]>C1COCC1.O>[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15]([OH:17])=[O:16])=[CH:11][C:10]=1[CH2:19][O:20][CH3:21])[CH3:2]

참가 물질

5

반응물 2

HCID 168937Lithium hydroxide, monohydrateHCID 58554174Methyl 2'-ethyl-2-(methoxymethyl)-[1,1'-biphenyl]-4-carboxylate

생성물 1

HCID 594958092'-Ethyl-2-(methoxymethyl)-[1,1'-biphenyl]-4-carboxylic acid수율 80%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of methyl 2′-ethyl-2-(methoxymethyl)-1,1′-biphenyl-4-carboxylate (12.0 g, 42.2 mmol) in THF (150 mL) and water (30 mL), was added lithium hydroxide monohydrate (5.31 g, 126.6 mmol) in portions. After 12 hours at RT, the reaction mixture was concentrated and the aqueous phase was acidified with a concentrated aqueous solution of HCl and extracted with EtOAc. The organic layers were washed with water and brine. The solvents were dried over sodium sulphate and concentrated under reduced pressure to afford the title compound as a white solid (9.0 g, 80%). 1H NMR (DMSO-d6, 300 MHz) δ 12.9 (1H, bs), 8.08 (1H, s), 7.89 (1H, m), 7.35 (2H, m), 7.23 (2H, m), 7.04 (1H, m), 4.04-4.13 (2H, m), 3.17 (3H, s), 2.29-2.38 (1H, m), 2.22 (1H, m), 0.94 (3H, m). LC/MS (Method A): 269.0 (M−H)−. HPLC (Method B) Rt 5.06 min (Purity: 97.4%).

후처리

  1. concentrationthe reaction mixture was concentrated
  2. extractionextracted with EtOAc
  3. washThe organic layers were washed with water and brine
  4. dry with materialThe solvents were dried over sodium sulphate
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-e046387d81c84fa78057fd9b701b6bb7
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08815919B2

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