Hydrochloric Acid → 1,4-Anhydro-2,5-dideoxy-2-(methoxycarbonyl)-1-thiopent-3-ulose

HRID 595066노트

반응식

HRID 595066 반응식
C(O[C:4](=[O:14])[CH:5]([S:7][CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH3:6])C.C[O-].[Na+].Cl>CO>[CH3:6][CH:5]1[S:7][CH2:8][CH:9]([C:10]([O:12][CH3:13])=[O:11])[C:4]1=[O:14]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 20472469Ethyl 2-[(3-methoxy-3-oxopropyl)sulfanyl]propanoate

생성물 1

HCID 126586981,4-Anhydro-2,5-dideoxy-2-(methoxycarbonyl)-1-thiopent-3-ulose수율 50%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of methyl 3-(2-ethoxy-1-methyl-2-oxo-ethyl)sulfanylpropanoate (2.2 g, 10 mmol) in methanol (15 mL) at 0° C. was added sodium methoxide (886 mg, 16.4 mmol). The reaction was warmed to rt and stirred for 3 h. The mixture was acidified with 1 N HCl to pH 2 and extracted with DCM. The organic phase was washed with water and brine, dried (Na2SO4), concentrated and purified by column chromatography, eluting with EtOAc in petroleum (3%-10%) to give methyl tetrahydro-5-methyl-4-oxothiophene-3-carboxylate as a colourless oil (0.85 g, 50% yield).

후처리

  1. extractionextracted with DCM
  2. washThe organic phase was washed with water and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. custompurified by column chromatography
  6. washeluting with EtOAc in petroleum (3%-10%)

출처 및 근거

ORD 기록
ord-cc00fb1b042c4d248b89fc855f5102f8
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242993B2

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