Hydrochloric Acid → 3-Oxo-2-oxabicyclo[2.2.1]heptane-5-carboxylic acid

HRID 1429131ノート

反応式

HRID 1429131 の反応式
[OH-].[Na+].C[O:4][C:5]([CH:7]1[CH2:11][CH:10](O)[CH2:9][CH:8]1[C:13]([O:15]C)=[O:14])=[O:6].Cl>CO>[O:14]=[C:13]1[CH:8]2[CH2:9][CH:10]([CH2:11][CH:7]2[C:5]([OH:4])=[O:6])[O:15]1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 5601004-Hydroxy-cyclopentane-1,2-dicarboxylic acid, dimethyl ester

生成物 1

HCID 462449653-Oxo-2-oxabicyclo[2.2.1]heptane-5-carboxylic acid収率 89.3%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Sodium hydroxide (1M, 74 mL, 0.074 mol) was added to a stirred solution of compound 3a (3.73 g, 0.018 mol) in methanol (105 mL) at room temperature. After 4 h, the reaction mixture was neutralized with 3M HCl, evaporated and co-evaporated with toluene several times. Pyridine (75 mL) and Ac2O (53 mL) were added and the reaction mixture was allowed to shake overnight at room temperature. The mixture was then co-evaporated with toluene and purified by flash column chromatography (ethyl acetate+1% acetic acid) which gave the title compound (2.51 g, 88%) as a yellow oil.

後処理

  1. customevaporated
  2. additionPyridine (75 mL) and Ac2O (53 mL) were added
  3. waitto shake overnight at room temperature
  4. custompurified by flash column chromatography (ethyl acetate+1% acetic acid) which

出典と根拠

ORDレコード
ord-cd29ad04fccf4828ada64ad263198fd2
出典データセット
uspto-grants-2015_01
特許番号
US08937080B2

反応ノート

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