Sodium Hydroxide → Cyclohexyl-hydroxy-thiophen-2-yl-acetic acid

HRID 2240305ノート

反応式

HRID 2240305 の反応式
C([O:3][C:4](=[O:18])[C:5]([CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)([OH:11])[C:6]1[S:7][CH:8]=[CH:9][CH:10]=1)C.[OH-].[Na+]>CO.C1COCC1>[CH:12]1([C:5]([OH:11])([C:6]2[S:7][CH:8]=[CH:9][CH:10]=2)[C:4]([OH:18])=[O:3])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 44147725Ethyl cyclohexyl(hydroxy)(thiophen-2-yl)acetate

生成物 1

HCID 13063448Cyclohexyl-hydroxy-thiophen-2-yl-acetic acid

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of cyclohexyl-hydroxy-thiophen-2-yl-acetic acid ethyl ester (361.8 g, 1.35 mol) in MeOH (1.5 litres) and THF (1.5 litres) is treated portionwise with 2M NaOH (1.1 litres) over 30 minutes. The reaction mixture is stirred at room temperature overnight and then concentrated in vacuo to remove the organic solvents. The remaining aqueous portion is partitioned between EtOAc (2 litres) and 20% citric acid in water (1 litre). The organic layer is separated, washed with brine and concentrated in vacuo to afford the titled compound which is used crude in the next step.

後処理

  1. concentrationconcentrated in vacuo
  2. customto remove the organic solvents
  3. customThe remaining aqueous portion is partitioned between EtOAc (2 litres) and 20% citric acid in water (1 litre)
  4. customThe organic layer is separated
  5. washwashed with brine
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-e8e477659825406fb04e1969b61792d9
出典データセット
uspto-grants-2010_05
特許番号
US07723356B2

反応ノート

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