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

HRID 1778347
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HRID 1778347 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 86684730Methyl 6-(benzenesulfonylmethyl)-3-(2-formylfuran-3-yl)-2-hydroxybenzoate2회

생성물 1

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

시약·촉매·용매 3

HCID 887Methanol용매
HCID 962Water용매
HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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%

출처 및 근거

ORD 기록
ord-6d76f35165aa45299da928e0c9c3b842
출처 데이터셋
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09266896B2

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