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

HRID 888213ノート

反応式

HRID 888213 の反応式
[CH2:1]([C@H:8]([C@H:12]([OH:16])[C:13]([OH:15])=[O:14])[C:9]([OH:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO[C:19](OC)([CH3:21])[CH3:20]>CC(C)=O.[Cu](Cl)Cl>[CH3:20][C:19]1([CH3:21])[O:16][C@@H:12]([C@@H:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:9]([OH:11])=[O:10])[C:13](=[O:15])[O:14]1

参加物

5

反応物 2

HCID 64952,2-DimethoxypropaneHCID 54300227(2R,3S)-2-benzyl-3-hydroxysuccinic acid

生成物 1

HCID 58488000(2R)-2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]-3-phenylpropanoic acid収率 72.9%

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-benzyl-3-hydroxysuccinic acid (1.70 g; 7.58 mmol; 1.0 eq.) in acetone (50.0 mL) was added 2,2-dimethoxypropane (1.86 g; 15.2 mmol; 2.0 eq.) and copper(II) chloride (102 mg; 0.76 mmol; 0.1 eq.). The resulting reaction mixture was stirred for 2 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 as a greenish oil (1.46 g) 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-a3d38328451c48bf9b632a80efed669f
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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