Methyl iodide → Methyl 3-methyl-4-oxooxane-3-carboxylate

HRID 736779노트

반응식

HRID 736779 반응식
[O:1]=[C:2]1[CH2:7][CH2:6][O:5][CH2:4][CH:3]1[C:8]([O:10][CH3:11])=[O:9].O[C:13]1CCOCC=1C(OC)=O.[H-].[Na+].IC>CN(C=O)C.C(OCC)(=O)C>[CH3:13][C:3]1([C:8]([O:10][CH3:11])=[O:9])[C:2](=[O:1])[CH2:7][CH2:6][O:5][CH2:4]1

참가 물질

7

반응물 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 14666555Methyl 4-oxooxane-3-carboxylateHCID 68541653methyl 4-hydroxy-5,6-dihydro-2H-pyran-3-carboxylate

생성물 1

HCID 68819284Methyl 3-methyl-4-oxooxane-3-carboxylate수율 61%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

Methyl 4-oxo-tetrahydro-2H-pyran-3-carboxylate and methyl 4-hydroxy-5,6-dihydro-2H-pyran-3-carboxylate (13.5 g, 85.5 mmol) were dissolved in DMF (70 mL). Sodium hydride (60%, 3.6 g, 1.05 eq) was added at 0° C. After 10 min, iodomethane (6.7 mL, 1.25 eq) was added. The reaction was stirred overnight, diluted with ethyl acetate (200 mL), and washed with water (5×100 mL). The aqueous layer was re-extracted with ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4, and concentrated. The residue was purified by chromatography on silica gel eluting with 20% ethyl acetate/hexane to yield 8.2 g (61%) of methyl 3-methyl-4-oxo-tetrahydro-2H-pyran-3-carboxylate.

후처리

  1. washwashed with water (5×100 mL)
  2. extractionThe aqueous layer was re-extracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on silica gel eluting with 20% ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-4436b5a6cbe04081ab88f5302356c23f
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07595327B2

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