海萝胶 → 6-Hydroxy-2-methyl-2,3-dihydro-1h-inden-1-one

HRID 37694

反应方程式

HRID 37694 反应方程式
[Br-].[Al+3].[Br-].[Br-].C[O:6][CH:7]1[CH2:15]C2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]1=O.ClCCl.C([O:23][CH2:24][CH3:25])(=O)C.Cl>C1C=CC=CC=1>[OH:6][C:7]1[CH:15]=[C:25]2[C:10]([CH2:11][CH:12]([CH3:13])[C:24]2=[O:23])=[CH:9][CH:8]=1

参与物

6

反应物 4

HCID 313海萝胶HCID 166749溴化羟铝HCID 10866644Methoxy indanoneHCID 21226138Dichloromethane ethylacetate

产物 1

HCID 2343386-Hydroxy-2-methyl-2,3-dihydro-1h-inden-1-one

试剂、催化剂与溶剂 1

HCID 241苯溶剂2 次

实验过程

To a stirred solution of anhydrous aluminum bromide (69.82 g, 0.261 mole) in anhydrous benzene (250 mL) kept under nitrogen is added dropwise over 30 minutes a solution of the methoxy indanone (18 g, 0.102 mole) of Step C, in benzene (60 mL). The mixture is gently refluxed for 3 hours (TLC, dichloromethane-ethyl acetate 8:2, UV), cooled in an ice bath and treated dropwise with 6N-HCl (ca. 200 mL) to decompose the aluminum complex. The aqueous phase is extracted with ether (3 times), the extracts are concentrated at reduced pressure and extracted with 2.5N-NaOH (2×75 mL and 1×50 mL). The basic extracts are neutralized (ice bath) with concentrated HCl and the oil that separates is extracted with ether (3 times). The combined extracts are washed with brine, dried (MgSO4) and evaporated to yield an oil that readily solidifies. The crude material is flash chromatographed (on silica Merck-60, gradient CH2Cl2, CH2Cl2 -ethyl acetate 85:15 ) to provide the pure title compound (13.60 g, nearly colorless solid, 82%).

后处理

  1. temperaturecooled in an ice bath
  2. extractionThe aqueous phase is extracted with ether (3 times)
  3. concentrationthe extracts are concentrated at reduced pressure
  4. extractionextracted with 2.5N-NaOH (2×75 mL and 1×50 mL)
  5. extractionthe oil that separates is extracted with ether (3 times)
  6. washThe combined extracts are washed with brine
  7. dry with materialdried (MgSO4)
  8. customevaporated
  9. customto yield an oil that
  10. customchromatographed (on silica Merck-60, gradient CH2Cl2, CH2Cl2 -ethyl acetate 85:15 )

来源与证据

ORD记录
ord-f438f32912d145acbeea5072e94ba4fd
来源数据集
uspto-grants-1995_05
专利号
US05420289

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