Acetic Acid → 5-[4-(2-Hydroxy-2-phenylethoxy)benzyl]-1,3-thiazolidine-2,4-dione

HRID 2274324

反応式

HRID 2274324 の反応式
[OH:1][CH:2]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:3][O:4][C:5]1[CH:18]=[CH:17][C:8]([CH:9]=[C:10]2[S:14][C:13](=[O:15])[NH:12][C:11]2=[O:16])=[CH:7][CH:6]=1.O.[BH4-].[Na+].C(O)(=O)C>C1COCC1.[OH-].[Na+].O.O.O.O.O.O.[Co](Cl)Cl.CC(=NO)C(C)=NO>[OH:1][CH:2]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[CH2:3][O:4][C:5]1[CH:18]=[CH:17][C:8]([CH2:9][CH:10]2[S:14][C:13](=[O:15])[NH:12][C:11]2=[O:16])=[CH:7][CH:6]=1

参加物

9

反応物 4

HCID 176Acetic Acid2 回HCID 962WaterHCID 4311764Sodium borohydride3 回HCID 866450705-[4-(2-Hydroxy-2-phenylethoxy)benzylidene]-1,3-thiazolidine-2,4-dione

生成物 1

HCID 469110415-[4-(2-Hydroxy-2-phenylethoxy)benzyl]-1,3-thiazolidine-2,4-dione収率 76.3%

試薬・触媒・溶媒 4

HCID 517166Dichlorocobalt hexahydrate触媒HCID 135459645Dimethylglyoxime触媒HCID 8028Tetrahydrofuran溶媒HCID 14798Sodium Hydroxide溶媒2 回

実験手順

To a mixture of 5-[4-(2-hydroxy-2-phenylethoxy)benzylidene]-1,3-thiazolidine-2,4-dione (1.50 g, 4.39 mmol) in THF (20 mL) was added H2O (20 mL), 1M NaOH (3 mL), cobalt (II) chloride hexahydrate (0.60 mg, 0.003 mmol) and dimethylglyoxime (15 mg, 0.13 mmol). A solution of sodium tetrahydroborate (240 mg, 6.33 mmol) in 0.2M NaOH (3.6 mL) was added. The reaction mixture immediately turned dark but very soon assumed a clear yellow appearance. Acetic acid was added dropwise until the solution turned dark (3 drops). After ca. one hour, the reaction lightened. Additional NaBH4, CoCl2 and HOAc were added to produce a deep blue-purple color. When that color faded, more NaBH4 was added. When HPLC analysis indicated that the reaction was complete, it was partitioned between H2O and EtOAc, and the organic phase was washed with brine, dried (Na2SO4), filtered and evaporated in vacuo. The resulting foamy solid was chromatographed, eluting with 50% EtOAc/hexanes. Fractions containing product were combined and evaporated in vacuo to give 1.15 g (76%) of the title compound as a white solid. MS (ESI−) for C18H17NO4S m/z 342.1 (M−H)−.

後処理

  1. customthe reaction lightened
  2. customto produce a deep blue-purple color
  3. customit was partitioned between H2O and EtOAc
  4. washthe organic phase was washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe resulting foamy solid was chromatographed
  9. washeluting with 50% EtOAc/hexanes
  10. additionFractions containing product
  11. customevaporated in vacuo

出典と根拠

ORDレコード
ord-5f327027b8384e5584d76ccfcb079674
出典データセット
uspto-grants-2015_09
特許番号
US09126959B2

関連ノート

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