Cycloate → 6-Methoxy-1-oxaspiro[2,5]octane

HRID 1809363

반응식

HRID 1809363 반응식
[H-].[Na+].[I-].C[S+](C)(C)=O.[CH3:9][O:10][CH:11]1[CH2:16][CH2:15][C:14](=[O:17])[CH2:13][CH2:12]1.[CH3:18]CN(C(SCC)=O)C1CCCCC1>CS(C)=O.O>[CH3:9][O:10][CH:11]1[CH2:16][CH2:15][C:14]2([O:17][CH2:18]2)[CH2:13][CH2:12]1

참가 물질

7

반응물 4

HCID 14337CycloateHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 5350284-Methoxycyclohexanone

생성물 1

HCID 153294906-Methoxy-1-oxaspiro[2,5]octane

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매2회HCID 962Water용매

실험 절차

To a stirred suspension of sodium hydride (60% in mineral oil, 1.20 g, 30.0 mmol) in dimethylsulfoxide (19 mL) was added trimethylsulfoxonium iodide (6.89 g, 31.3 mmol) at room temperature, and the mixture was stirred at room temperature for 30 min. To this mixture was added a solution of 4-methoxycyclohexanone (3.53 g, 10.0 mmol, prepared according to Shvily, Ronit et al., J. Chem. Soc. Perkin Trans. 2, 1997, 6, 1221) in dimethylsulfoxide (95 mL) dropwise at room temperature, and the mixture was stirred at room temperature for 20 h. Then the mixture was diluted with water (1.0 L), and extracted with diethyl ether (200 mL×6). The combined organic layers were dried over magnesium sulfate, and concentrated in vacuo. The residue was chromatographed on a column of silica gel eluting n-hexane/ethyl acetate (v/v=15/1˜10/1) to give 338 mg (9%, cis) and 204 mg (5%, trans) of the title compound as colorless oil respectively.

후처리

  1. customprepared
  2. extractionextracted with diethyl ether (200 mL×6)
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on a column of silica gel
  6. washeluting n-hexane/ethyl acetate (v/v=15/1˜10/1)

출처 및 근거

ORD 기록
ord-c7b290177d6340a1b494980bf6f5a1b5
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362038B2

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