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Ethyl Acetate → Methyl 6-(benzenesulfonylmethyl)-2-hydroxy-3-(2-hydroxymethylfuran-3-yl)-benzoate

HRID 1778347
ノート
印刷プレビュー

反応式

HRID 1778347 の反応式
[BH4-].[Na+].[C:3]1([S:9]([CH2:12][C:13]2[C:18]([C:19]([O:21][CH3:22])=[O:20])=[C:17]([OH:23])[C:16]([C:24]3[CH:28]=[CH:27][O:26][C:25]=3[CH:29]=[O:30])=[CH:15][CH:14]=2)(=[O:11])=[O:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Cl-].[NH4+].C(OCC)(=O)C>CO.C1COCC1.O>[C:3]1([S:9]([CH2:12][C:13]2[C:18]([C:19]([O:21][CH3:22])=[O:20])=[C:17]([OH:23])[C:16]([C:24]3[CH:28]=[CH:27][O:26][C:25]=3[CH2:29][OH:30])=[CH:15][CH:14]=2)(=[O:11])=[O:10])[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 86684730Methyl 6-(benzenesulfonylmethyl)-3-(2-formylfuran-3-yl)-2-hydroxybenzoate2 回

生成物 1

HCID 66685310Methyl 6-(benzenesulfonylmethyl)-2-hydroxy-3-(2-hydroxymethylfuran-3-yl)-benzoate収率 96.5%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒
HCID 962Water溶媒
HCID 8028Tetrahydrofuran溶媒

実験手順

Sodium borohydride (0.031 g) was added to a solution of methyl 6-(benzenesulfonylmethyl)-3-(2-formylfuran-3-yl)-2-hydroxybenzoate (Intermediate 28, 0.67 g) in methanol (6 mL) and THF (12 mL) at 0° C. and the resultant mixture was stirred at 0° C. for 10 minutes. Saturated aqueous ammonium chloride, ethyl acetate and water were added and the organic layer was separated, washed with brine, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 30-80% to give methyl 6-(benzenesulfonylmethyl)-2-hydroxy-3-(2-hydroxymethylfuran-3-yl)-benzoate (0.65 g) as a white solid.

後処理

  1. customthe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness
  6. customthe residue was purified by chromatography on silica
  7. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 30-80%

出典と根拠

ORDレコード
ord-6d76f35165aa45299da928e0c9c3b842
出典データセット
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09266896B2

反応ノート

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