Sulfuric Acid → Ethyl 4-bromo-3-oxocyclohexanecarboxylate

HRID 1593613노트

반응식

HRID 1593613 반응식
[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]

참가 물질

6

반응물 3

HCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 58999614HCID 58999614, 화합물

생성물 1

HCID 12917736Ethyl 4-bromo-3-oxocyclohexanecarboxylate

시약·촉매·용매 2

HCID 180Acetone용매HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1aa439f5d3704070b1ba649c12a848de
출처 데이터셋
uspto-grants-2007_11
특허 번호
US07297704B2

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