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

HRID 1677766ノート

反応式

HRID 1677766 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 14325352(2S,3R)-2-hydroxy-3-methylbutanedioic acid

生成物 1

HCID 58488031(2R)-2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]propanoic acid収率 82%

試薬・触媒・溶媒 2

HCID 24014Cupric Chloride触媒HCID 180Acetone溶媒

実験手順

To a solution of (2S,3R)-2-hydroxy-3-methylsuccinic acid (2.40 g; 16.2 mmol; 1.0 eq.) in acetone (80.0 mL) was added 2,2-dimethoxypropane (3.98 g; 32.4 mmol; 2.0 eq.) and copper(II) chloride (218 mg; 1.62 mmol; 0.1 eq.). The resulting reaction mixture was stirred for 4 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 diastereoisomers) as a greenish oil (2.48 g, 82%) 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-168aa7734ff547db816b722a133cb381
出典データセット
uspto-grants-2011_08
特許番号
US08008302B2

反応ノート

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