Isopropanol → (S)-methyl 2-hydroxy-3-isopropoxypropanoate

HRID 1098107

反応式

HRID 1098107 の反応式
[O:1]1[CH2:3][C@H:2]1[C:4]([O:6][CH3:7])=[O:5].FC(F)(F)S([O-])(=O)=O.[Mg+2].FC(F)(F)S([O-])(=O)=[O:20].[CH3:25][CH:26](O)[CH3:27]>C(OCC)(=O)C>[OH:20][C@@H:2]([CH2:3][O:1][CH:26]([CH3:27])[CH3:25])[C:4]([O:6][CH3:7])=[O:5]

参加物

5

反応物 3

HCID 3776IsopropanolHCID 2734125Magnesium trifluoromethanesulfonateHCID 10942355Methyl (2S)-2-oxiranecarboxylate

生成物 1

HCID 59279510(S)-methyl 2-hydroxy-3-isopropoxypropanoate収率 302.1%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒2 回

実験手順

(S)-Methyl oxirane-2-carboxylate (2.04 g, 19.98 mmol), magnesium trifluoromethanesulfonate (1.611 g, 5.00 mmol) and propan-2-ol (1.84 mL, 24.0 mmol) in ethyl acetate (10 mL) were heated at reflux for 90 hours. The mixture was diluted with EtOAc (20 mL), filtered and evaporated. The residue was purified by flash silica chromatography, elution gradient 20 to 50% EtOAc in isohexane to afford (S)-methyl 2-hydroxy-3-isopropoxypropanoate (2.45 g, 76%). 1H NMR (400 MHz, CDCl3) δ 1.13 (3H, d), 1.16 (3H, d), 3.00 (1H, d), 3.58-3.64 (1H, m), 3.68-3.74 (2H, m), 3.69-3.73 (1H, m), 3.80 (3H, s), 4.28-4.31 (1H, m)

後処理

  1. temperatureat reflux for 90 hours
  2. filtrationfiltered
  3. customevaporated
  4. customThe residue was purified by flash silica chromatography, elution gradient 20 to 50% EtOAc in isohexane

出典と根拠

ORDレコード
ord-4d1a56a56df94e5dabaf003a261013f7
出典データセット
uspto-grants-2012_03
特許番号
US08143263B2

関連ノート

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