Water → Benzyl 1-methyl-4-oxocyclohexane-1-carboxylate

HRID 1968986

반응식

HRID 1968986 반응식
C[Si](C)(C)O[CH:4]=[CH:5][CH:6]=[CH2:7].[CH3:10][C:11](=[CH2:22])[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13].[OH2:23]>C(C1C=C(C(C)(C)C)C(O)=C(C(C)(C)C)C=1)C1C=C(C(C)(C)C)C(O)=C(C(C)(C)C)C=1>[CH3:22][C:11]1([C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[CH2:7][CH2:6][C:5](=[O:23])[CH2:4][CH2:10]1

참가 물질

5

반응물 3

HCID 962WaterHCID 17236Benzyl methacrylateHCID 27242171-(Trimethylsiloxy)-1,3-butadiene

생성물 1

HCID 59444129Benzyl 1-methyl-4-oxocyclohexane-1-carboxylate수율 24.89%

시약·촉매·용매 1

HCID 83724,4'-Methylenebis(2,6-di-tert-butylphenol)촉매

반응 조건

온도
200 °C

실험 절차

2-(Trimethylsilyloxybutadiene (6.46 g, 45.4 mmol), phenylmethyl 2-methyl-2-propenoate (8.00 g, 45.4 mmol), and 4,4′-methanediylbis[2,6-bis(1,1-dimethylethyl)phenol] (0.019 g, 0.045 mmol) were combined together in a 20.0 mL microwave vessel and heated to 200° C. for 300 mins. Sample recovered and removed from vessel using THF (˜3×10 mL). The solvent was removed under reduced pressure and the residual oil taken up in 10% 2N HCl/THF (100 mL) and stirred overnight. After this time a clear solution formed, which was diluted with water (50 mL), partitioned into DCM (2×100 mL) and the organic layers separated, dried over MgSO4, filtered and the solvent removed under reduced pressure. The residue was purified by FC over Silica (150 g: 5-10% EtOAc/iso-hex) to afford a clear oil. Confirmed by NMR to be phenylmethyl 1-methyl-4-oxocyclohexanecarboxylate (3.48 g, 11.30 mmol, 24.89% yield).

후처리

  1. customSample recovered
  2. customremoved from vessel
  3. customThe solvent was removed under reduced pressure
  4. customAfter this time a clear solution formed
  5. custompartitioned into DCM (2×100 mL)
  6. customthe organic layers separated
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customthe solvent removed under reduced pressure
  10. customThe residue was purified by FC over Silica (150 g: 5-10% EtOAc/iso-hex)
  11. customto afford a clear oil

출처 및 근거

ORD 기록
ord-ec0c866b03c24aa4863501511263fac8
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08426443B2

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