Acetic Acid → Methyl 5,6-dihydro-2H-thiopyran-3-carboxylate

HRID 1267674ノート

反応式

HRID 1267674 の反応式
[S:1]1[CH2:6][CH2:5][CH:4]=[C:3]([C:7]([O-:9])=[O:8])[CH2:2]1.B(O[O-])=O.[Na+].O.[OH-].[Na+].[C:18](O)(=O)C>>[S:1]1[CH2:6][CH2:5][CH:4]=[C:3]([C:7]([O:9][CH3:18])=[O:8])[CH2:2]1

参加物

6

反応物 5

HCID 176Acetic AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 517072Sodium PerborateHCID 219460775,6-dihydro-2H-thiopyran-3-carboxylate

生成物 1

HCID 10351950Methyl 5,6-dihydro-2H-thiopyran-3-carboxylate収率 76%

反応条件

温度
55 °C

実験手順

To a solution of 0.934 gm (5.75 mmol) of 5,6-dihydro-2H-thiopyran-3-carboxylate from part C in glacial acetic acid (40 mL) was added 1.98 gm (12.88 mmole) sodium perborate. The reaction mixture was stirred at 55° C. under N2 for 19 hrs. whereupon the solution was poured into H2O (50 mL) and neutralized with 50% NaOH to pH=7. The solution was extracted three times with methylene chloride. The combined organic layers were washed once with saturated sodium bicarbonate and once with saturated sodium chloride, dried over magnesium sulfate, filtered and concentrated in vacuo to give 0.832 gm (76%) of methyl 5,6-dihydro-2H-thiopyran-3-carboxylate, 1,1 dioxide as a white solid; mass spectrum m/e=190 (EI, M+)

後処理

  1. extractionThe solution was extracted three times with methylene chloride
  2. washThe combined organic layers were washed once with saturated sodium bicarbonate and once with saturated sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-72c3f34b0e274cad80cc863990418164
出典データセット
uspto-grants-2003_04
特許番号
US06552203B2

反応ノート

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