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

HRID 1630972ノート

反応式

HRID 1630972 の反応式
O.[OH-].[Li+].[CH2:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[CH:17]=[CH:16][C:15]([C:18]([O:20]C)=[O:19])=[CH:14][C:13]=1[CH2:22][O:23][CH3:24])[CH3:5]>C1COCC1.O>[CH2:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[CH:17]=[CH:16][C:15]([C:18]([OH:20])=[O:19])=[CH:14][C:13]=1[CH2:22][O:23][CH3:24])[CH3:5]

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

Lithium hydroxide monohydrate (5.31 g, 127 mmol) was added portion-wise into 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). The resulting mixture was stirred at RT for 12 hours. The reaction mixture was concentrated under reduced pressure. The resulting aqueous layer was acidified with a concentrated aqueous solution of HCl and extracted with EtOAc. The organic layers were washed with water and brine, combined and dried (Na2SO4). The solvents were removed under reduced pressure to afford the title compound as a white solid (9.0 g, 80%). HPLC (Method A), Rt 4.2 min (purity: 96.7%). UPLC/MS, M−(ESI): 269.2. 1H NMR (DMSO-d6, 400 MHz) δ 12.9 (1H, bs), 8.08 (1H, s), 7.89 (1H, d), 7.35 (2H, m), 7.23 (2H, m), 7.04 (1H, d), 4.09 (2H, m), 3.17 (3H, s), 2.34 (1H, m), 2.22 (1H, m), 0.94 (3H, t).

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionextracted with EtOAc
  3. washThe organic layers were washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. customThe solvents were removed under reduced pressure

出典と根拠

ORDレコード
ord-ce27f29ecc68466ca3adc85941a6cad4
出典データセット
uspto-grants-2014_07
特許番号
US08791142B2

反応ノート

読み込み中…