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

HRID 1098107

반응식

HRID 1098107 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매2회

실험 절차

(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)

후처리

  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

출처 및 근거

ORD 기록
ord-4d1a56a56df94e5dabaf003a261013f7
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08143263B2

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