2,2-Dimethoxypropane → (2S)-2-[(4R)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]propanoic acid

HRID 888210ノート

反応式

HRID 888210 の反応式
[OH:1][C@H:2]([C@H:6]([CH3:10])[C:7]([OH:9])=[O:8])[C:3]([OH:5])=[O:4].CO[C:13](OC)([CH3:15])[CH3:14]>CC(C)=O.[Cu](Cl)Cl>[CH3:14][C:13]1([CH3:15])[O:1][C@H:2]([C@H:6]([CH3:10])[C:7]([OH:9])=[O:8])[C:3](=[O:5])[O:4]1

参加物

5

反応物 2

HCID 64952,2-DimethoxypropaneHCID 440892D-Erythro-3-Methylmalate

生成物 1

HCID 58488020(2S)-2-[(4R)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]propanoic acid収率 59%

試薬・触媒・溶媒 2

HCID 24014Cupric Chloride触媒HCID 180Acetone溶媒

実験手順

To a solution of (2R,3S)-2-hydroxy-3-methylsuccinic acid (2.48 g; 16.8 mmol; 1.0 eq.) in acetone (80.0 mL) was added 2,2-dimethoxypropane (4.13 g; 33.6 mmol; 2.0 eq.) and copper(II) chloride (226 mg; 1.68 mmol; 0.1 eq.). The resulting reaction mixture was stirred for 16 h at RT. The reaction mixture was evaporated and the residue taken up in CHCl3. Activated charcoal is added and the resulting mixture stirred for one hour. Filtration on a pad of celite gave the title product (mixture of diatereoisomers) as a greenish oil (1.85 g, 59%) used in the next step without further purification.

後処理

  1. customThe resulting reaction mixture
  2. customThe reaction mixture was evaporated
  3. additionActivated charcoal is added
  4. stirringthe resulting mixture stirred for one hour
  5. filtrationFiltration on a pad of celite

出典と根拠

ORDレコード
ord-378a66eedbe44765a7ccdb211cbcc7f1
出典データセット
uspto-grants-2012_08
特許番号
US08247437B2

反応ノート

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