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

HRID 219827ノート

反応式

HRID 219827 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 g, 0.0422 mol) in THF (150 mL) and water (30 mL), was added lithium hydroxide monohydrate (5.31 g, 0.1266 mol) in portions. After 12 h at RT, the reaction mixture was concentrated and the aqueous phase was acidified using conc. HCl and extracted with EtOAc. Then the organic layers were washed with water and brine solution. The solvents were dried over sodium sulphate and concentrated under reduced pressure to afford the title compound as a white solid (9 g, 80%). 1H NMR (DMSO-d6, 300 MHz) δ 12.9 (1H, bs), 8.08 (1H, s), 7.88-7.90 (1H, m), 7.34-7.35 (2H, m), 7.21-7.25 (2H, m), 7.03-7.05 (1H, m), 4.04-4.13 (2H, m), 3.16-3.18 (3H, s), 2.29-2.38 (1H, m), 2.19-2.24 (1H, m), 0.92-0.95 (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. washThen the organic layers were washed with water and brine solution
  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-b78b0999bdc24027b7c6a6db89369f70
出典データセット
uspto-grants-2012_06
特許番号
US08202865B2

反応ノート

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