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Water → ethyl 4-oxo-5,6,7,8-tetrahydro-4H-cyclohepta[b]furan-3-carboxylate

HRID 1290086
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HRID 1290086 반응식
CS(Cl)(=O)=O.O[C:7]1([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:11][O:10][C:9]2[CH2:12][CH2:13][CH2:14][CH2:15][C:16](=[O:17])[C:8]1=2.C(N(CC)CC)C.O>ClCCl>[O:17]=[C:16]1[C:8]2[C:7]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:11][O:10][C:9]=2[CH2:12][CH2:13][CH2:14][CH2:15]1
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6

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HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 18696566ethyl 3-hydroxy-4-oxo-2,3,5,6,7,8-hexahydro-4H-cyclohepta[b]furan-3-carboxylate

생성물 1

HCID 18696560ethyl 4-oxo-5,6,7,8-tetrahydro-4H-cyclohepta[b]furan-3-carboxylate

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

Methanesulfonyl chloride (9.7 g, 0.08 mol) was added dropwise to a stirring solution of ethyl 3-hydroxy-4-oxo-2,3,5,6,7,8-hexahydro-4H-cyclohepta[b]furan-3-carboxylate (17 g, 0.07 mol) and triethylamine (30 mL, 0.21 mol) in dichloromethane (100 mL) at 0° C. The mixture was allowed to reach ambient temperature, stirred for 2 hours, then poured into water and extracted with dichloromethane. The organic layer was washed sequentially with aqueous 2N sodium hydroxide, saturated aqueous sodium bicarbonate, and brine, then dried over magnesium sulfate, filtered, concentrated in vacuo, and purified on Silica gel (1:1 ethyl acetate/hexanes) to give the title compound.

후처리

  1. customto reach ambient temperature
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed sequentially with aqueous 2N sodium hydroxide, saturated aqueous sodium bicarbonate, and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. custompurified on Silica gel (1:1 ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-085c137279374d3d9603603b96207c47
출처 데이터셋
uspto-grants-1998_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05750702

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