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

HRID 2410482ノート

反応式

HRID 2410482 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-e046387d81c84fa78057fd9b701b6bb7
出典データセット
uspto-grants-2014_08
特許番号
US08815919B2

反応ノート

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