Methyl 4-benzyloxythieno[2,3-c]pyridine-2-carboxylate → Methyl 4-hydroxythieno[2,3-c]pyridine-2-carboxylate

HRID 1977420ノート

反応式

HRID 1977420 の反応式
C([O:8][C:9]1[CH:14]=[N:13][CH:12]=[C:11]2[S:15][C:16]([C:18]([O:20][CH3:21])=[O:19])=[CH:17][C:10]=12)C1C=CC=CC=1.CC(C)=O.CCCCCC>C(O)C.[Pd]>[OH:8][C:9]1[CH:14]=[N:13][CH:12]=[C:11]2[S:15][C:16]([C:18]([O:20][CH3:21])=[O:19])=[CH:17][C:10]=12

参加物

5

反応物 2

HCID 18516285Methyl 4-benzyloxythieno[2,3-c]pyridine-2-carboxylateHCID 21880519Acetone hexane

生成物 1

HCID 18516273Methyl 4-hydroxythieno[2,3-c]pyridine-2-carboxylate収率 75%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒2 回HCID 702Ethanol溶媒2 回

実験手順

To a suspension of 10 wt % Pd on activated carbon (38 mg, 10% w/w) in absolute ethanol (3 mL) was added a cold solution of Example 236C (380 mg, 1.3 mmol) in ethanol (82 mL) under nitrogen atmosphere. Then the reaction mixture was degassed and stirred at room temperature under hydrogen atmosphere. After one over night reaction mixture was treated with additional 10 wt % Pd on activated carbon (190 mg, 50% w/w) and stirred under hydrogen atmosphere. Additional catalyst (100 mg, 26% w/w) was added to the reaction mixture after 48 hours. The reaction mixture was stirred under hydrogen atmosphere for further 24 hours and filtered through Celite®. The filtrate was evaporated to dryness under reduced pressure to obtain the crude product (320 mg). The title compound Example 236E was obtained in 75% yield (200 mg) by flash chromatography on silica gel eluting with 5% acetone-hexane followed by 40% acetone-hexane.

後処理

  1. customThen the reaction mixture was degassed
  2. customAfter one over night reaction mixture
  3. stirringstirred under hydrogen atmosphere
  4. additionAdditional catalyst (100 mg, 26% w/w) was added to the reaction mixture after 48 hours
  5. stirringThe reaction mixture was stirred under hydrogen atmosphere for further 24 hours
  6. filtrationfiltered through Celite®
  7. customThe filtrate was evaporated to dryness under reduced pressure
  8. customto obtain the crude product (320 mg)

出典と根拠

ORDレコード
ord-70835d03fb2e48658f95876644e9abca
出典データセット
uspto-grants-2001_05
特許番号
US06232320B1

反応ノート

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