Iodine → (1-Hydroxy-cyclohexyl)-acetic acid ethyl ester

HRID 550281

反応式

HRID 550281 の反応式
[C:1]1(=[O:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.II.Br[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].S(=O)(=O)(O)O>C1COCC1.[Zn]>[CH2:15]([O:14][C:12](=[O:13])[CH2:11][C:1]1([OH:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[CH3:16]

参加物

7

反応物 4

HCID 807IodineHCID 1118Sulfuric AcidHCID 7748Ethyl bromoacetateHCID 7967Cyclohexanone

生成物 1

HCID 219250(1-Hydroxy-cyclohexyl)-acetic acid ethyl ester収率 95.2%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of cyclohexanone (9.52 g, 97.0 mmol), a zinc powder (7.6 g, 116.4 mmol) and a small amount of iodine in THF (100 ml) was added dropwise ethyl bromoacetate (11.8 ml, 106.7 mmol) under a nitrogen atmosphere, and the mixture was heated under reflux for 5 hrs. 10% Sulfuric acid (100 ml) was carefully added under ice-cooling, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous MgSO4, and concentrated under reduced pressure to give the title compound (17.2 g, 94%) as a colorless oil.

後処理

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 hrs
  3. temperaturecooling
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution
  6. dry with materialdried over anhydrous MgSO4
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-d2e026c0189145f6877d14a4e2913dec
出典データセット
uspto-grants-2011_05
特許番号
US07943770B2

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