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

HRID 595066ノート

反応式

HRID 595066 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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).

後処理

  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%)

出典と根拠

ORDレコード
ord-cc00fb1b042c4d248b89fc855f5102f8
出典データセット
uspto-grants-2016_01
特許番号
US09242993B2

反応ノート

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