Sodium hydride → methyl 8-oxo-1,4-dioxaspiro[4.5]decane-7-carboxylate

HRID 602943노트

반응식

HRID 602943 반응식
[CH2:1]1[O:11][C:4]2([CH2:9][CH2:8][C:7](=[O:10])[CH2:6][CH2:5]2)[O:3][CH2:2]1.[H-].[Na+]>C(=O)(OC)OC.C1(C)C=CC=CC=1>[O:10]=[C:7]1[CH2:6][CH2:5][C:4]2([O:3][CH2:2][CH2:1][O:11]2)[CH2:9][CH:8]1[C:4]([O:3][CH3:2])=[O:11]

참가 물질

5

반응물 2

HCID 24758Sodium hydrideHCID 5674151,4-Dioxaspiro[4.5]decan-8-one

생성물 1

HCID 4088708methyl 8-oxo-1,4-dioxaspiro[4.5]decane-7-carboxylate

시약·촉매·용매 2

HCID 1140Toluene용매HCID 12021Dimethyl Carbonate용매

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온도
80 °C

실험 절차

To a stirred solution of 1,4-cyclohexanedione monoethylene ketal (1.00 g, 6.4 mmol) in dimethyl carbonate (6 mL) at room temperature was added sodium hydride (0.31 g, 7.7 mmol). The mixture was heated at 80° C. for 20 min and then diluted with dry toluene (20 mL). The mixture was stirred for an additional 3 h at 80° C., cooled to room temperature, quenched with water, and then extracted with dichloromethane. The organic phase was dried over anhydrous sodium sulfate and evaporated to yield the crude product which was purified by Biotage® chromatography (silica gel, ethyl acetate in hexanes gradient 30-42%) to yield the title compound.

후처리

  1. temperaturecooled to room temperature
  2. customquenched with water
  3. extractionextracted with dichloromethane
  4. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  5. customevaporated
  6. customto yield the crude product which
  7. customwas purified by Biotage® chromatography (silica gel, ethyl acetate in hexanes gradient 30-42%)

출처 및 근거

ORD 기록
ord-5eeefd47b207450798411773a097a846
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07906649B2

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