Sulfuric Acid → Ethyl 4-bromo-3-oxocyclohexanecarboxylate

HRID 1593613ノート

反応式

HRID 1593613 の反応式
[Br:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH:3]1[OH:13].OS(O)(=O)=O.C(O)(C)C>CC(C)=O.O>[Br:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][C:3]1=[O:13]

参加物

6

反応物 3

HCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 58999614HCID 58999614、化合物

生成物 1

HCID 12917736Ethyl 4-bromo-3-oxocyclohexanecarboxylate

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 962Water溶媒

実験手順

To a solution of ethyl 4-bromo-3-hydroxycyclohexanecarboxylate (15.06 g) in acetone (300 mL) at 0° C. was added CrO3 (12.0 g, 120 mmol), and 2 N H2SO4 (60 mL). The mixture was stirred at room temperature for 30 min. Isopropanol (15 mL) was added and the reaction was stirred for 20 min. The volume was reduced under vacuum then diluted with water and extracted with ethyl acetate. The organic layer was washed with water, then brine, was dried over MgSO4 and concentrated in vacuo. Purification by chromatography on silica gel (10% EtOAc in hexane) afforded 6.7 g of tide compound.

後処理

  1. stirringthe reaction was stirred for 20 min
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialbrine, was dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification by chromatography on silica gel (10% EtOAc in hexane)
  7. customafforded 6.7 g of tide compound

出典と根拠

ORDレコード
ord-1aa439f5d3704070b1ba649c12a848de
出典データセット
uspto-grants-2007_11
特許番号
US07297704B2

反応ノート

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