Dimethyl Sulfoxide → Ethyl 4-(1-oxaspiro[2.5]oct-6-yl)benzoate

HRID 1035706노트

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HRID 1035706 반응식
[H-].[Na+].[I-].C[S+](C)(C)=O.[CH3:9]S(C)=O.[O:13]=[C:14]1[CH2:19][CH2:18][CH:17]([C:20]2[CH:30]=[CH:29][C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:22][CH:21]=2)[CH2:16][CH2:15]1>CS(C)=O.C1COCC1.O>[O:13]1[C:14]2([CH2:19][CH2:18][CH:17]([C:20]3[CH:21]=[CH:22][C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:29][CH:30]=3)[CH2:16][CH2:15]2)[CH2:9]1

참가 물질

7

반응물 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 22633634Ethyl 4-(4-oxocyclohexyl)benzoate

생성물 1

HCID 86662113Ethyl 4-(1-oxaspiro[2.5]oct-6-yl)benzoate

시약·촉매·용매 2

HCID 962Water용매HCID 21830753dimethylsulfoxide THF용매2회

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온도
10 °C

실험 절차

0.246 g of sodium hydride (9.74 mmol, 2 eq.) is placed in 25 mL of a 1/1.5 mixture of THF/DMSO with stirring at 10° C. 2.14 g of trimethylsulfoxonium iodide (9.74 mmol, 1.2 eq.) are added. After 5 minutes, 10 mL of DMSO are added dropwise. After the evolution of gas has ceased, 2 g of ethyl 4-(4-oxocyclohexyl)benzoate (8.12 mmol, 1 eq.) dissolved in a minimum amount of a 2/1 mixture of DMSO/THF are rapidly added at room temperature. After stirring for 1 hour at room temperature and for 1 hour at 50° C., the reaction medium is diluted with 75 mL of water and extracted with ethyl acetate. The organic phases are successively washed twice with water and with brine, dried over sodium sulfate and evaporated. The residue is chromatographed on silica gel with a gradient of methanol in dichloromethane ranging from 1% to 2%. 1.8 g of ethyl 4-(1-oxaspiro[2.5]oct-6-yl)benzoate are obtained.

후처리

  1. additionare rapidly added at room temperature
  2. stirringAfter stirring for 1 hour at room temperature and for 1 hour at 50° C.
  3. extractionextracted with ethyl acetate
  4. washThe organic phases are successively washed twice with water and with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customThe residue is chromatographed on silica gel with a gradient of methanol in dichloromethane ranging from 1% to 2%

출처 및 근거

ORD 기록
ord-19d5df5b42d64e3c974ec66b1111d556
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546391B2

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