Acetate → 1-(1-Hydroxyethyl)-3-oxocyclopentanecarboxylic acid

HRID 643542ノート

反応式

HRID 643542 の反応式
C([O:4][CH:5]([C:7]1([C:16]([O:18]C(C)(C)C)=[O:17])[CH2:11][CH2:10][C:9](OC)([O:12]C)[CH2:8]1)[CH3:6])(=O)C.C([O-])(=O)C>Cl.O1CCOCC1.O>[OH:4][CH:5]([C:7]1([C:16]([OH:18])=[O:17])[CH2:11][CH2:10][C:9](=[O:12])[CH2:8]1)[CH3:6]

参加物

6

反応物 2

HCID 175AcetateHCID 68534118Tert-butyl 1-[1-(acetyloxy)ethyl]-3,3-dimethoxycyclopentanecarboxylate

生成物 1

HCID 578805271-(1-Hydroxyethyl)-3-oxocyclopentanecarboxylic acid

試薬・触媒・溶媒 3

HCID 313Hydrochloric Acid溶媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

tert-Butyl 1-[1-(acetyloxy)ethyl]-3,3-dimethoxycyclopentanecarboxylate (8.04 g, 25.4 mmol) was dissolved in anhydrous 4N HCl in dioxane (ca. 50 mL) and 5 mL of water was added (this was a mistake which led to inadvertent hydrolysis of the acetate). The reaction mixture was stirred at rt for 5 h, then was concentrated. Purification by flash chromatography (silica, 8% methanol/DCM) afforded 1-(1-hydroxyethyl)-3-oxocyclopentanecarboxylic acid.

後処理

  1. additionwas added (
  2. concentrationwas concentrated
  3. customPurification by flash chromatography (silica, 8% methanol/DCM)

出典と根拠

ORDレコード
ord-edfccfa2496b431c9033abe2df2c684c
出典データセット
uspto-grants-2010_04
特許番号
US07700591B2

反応ノート

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