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

HRID 2060031

反応式

HRID 2060031 の反応式
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

参加物

5

反応物 3

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

生成物 1

HCID 59444129Benzyl 1-methyl-4-oxocyclohexane-1-carboxylate収率 24.89%

試薬・触媒・溶媒 1

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

反応条件

温度
200 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-4577cba1a7964887a0e9fa342b134259
出典データセット
uspto-grants-2012_10
特許番号
US08278328B2

関連ノート

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