Bromide ion → Ethyl (2-methylidenecyclohexyl)acetate

HRID 1245410

反応式

HRID 1245410 の反応式
[Br-].[H-].[Na+].[CH2:4]([O:6][C:7](=[O:16])[CH2:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C:10]1=O)[CH3:5].[CH3:17]N(C=O)C>>[CH2:4]([O:6][C:7](=[O:16])[CH2:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C:10]1=[CH2:17])[CH3:5]

参加物

5

反応物 4

HCID 259Bromide ionHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 91229Ethyl 2-oxocyclohexylacetate

生成物 1

HCID 12679490Ethyl (2-methylidenecyclohexyl)acetate収率 50%

反応条件

温度
0 °C

実験手順

Triphenylphosphoniummethyl bromide (6.9 g, 19.5 mmol) was added to a suspension of sodium hydride (0.78 g, 60% oil dispersion, 19.5 mmol) (hexane washed) in DMF (50 mL) cooled to 0° C. under a nitrogen atmosphere. The reaction was stirred for 1 h, and then (2-oxo-cyclohexyl)-acetic acid ethyl ester (3.0 g, 16.2 mmol) was added. The reaction was allowed to warm to room temperature and stirred for 18 h. The reaction was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated to give a residue. The product was purified by FCC on silica gel eluting with hexane:ethyl acetate (95:5) to give (2-methylene-cyclohexyl)-acetic acid ethyl ester (1.5 g, 50%) as an oil.

後処理

  1. temperatureto warm to room temperature
  2. stirringstirred for 18 h
  3. customThe reaction was partitioned between ethyl acetate and water
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customto give a residue
  8. customThe product was purified by FCC on silica gel eluting with hexane:ethyl acetate (95:5)

出典と根拠

ORDレコード
ord-110b3519d490411c9150e1774e0cfb28
出典データセット
uspto-grants-2006_10
特許番号
US07125870B2

関連ノート

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