Tetrahydrofuran → HCID 69242505, compound

HRID 2371099Notes

Reaction equation

HRID 2371099 reaction equation
[C:1]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][C:9](=[O:18])[CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:3][CH:2]=1.O1CCCC1.CC(C)([O-])C.[K+].Br[CH2:37][CH2:38][N:39]1[C:44](=[O:45])[C:43]2[CH:46]=[CH:47][CH:48]=[CH:49][C:42]=2[N:41]=[N:40]1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C(O)(C)(C)C>[C:1]1([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:2]=[CH:3][C:4]([CH2:7][CH2:8][C:9](=[O:18])[CH:10]([CH2:37][CH2:38][N:39]2[C:44](=[O:45])[C:43]3[CH:46]=[CH:47][CH:48]=[CH:49][C:42]=3[N:41]=[N:40]2)[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:5][CH:6]=1

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 23665647Potassium tert-butoxideHCID 43589287HCID 43589287, compoundHCID 58914664Tert-butyl 5-biphenyl-4-yl-3-oxopentanoate

Product 1

HCID 69242505HCID 69242505, compoundYield 52.2%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

To a solution of the compound (300 mg) obtained from step 1 above in dry tetrahydrofuran (4 ml) and tert-butanol (4 ml) at 0° C. was added potassium tert-butoxide (104 mg) and stirred for 20 minutes. To the resulting reaction mixture was added 3-(2-bromoethyl)-1,2,3-benzotriazin-4(3H)-one (235 mg) and tetrabutylammonium iodide (349 mg) and the mixture was further stirred for 30 minutes at 0° C., followed by stirring at room temperature for 30 minutes and finally at 80° C. for about 5-6 hours. The solvent was evaporated under reduced pressure and the residue thus obtained was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulphate and filtered. The solvent was evaporated under reduced pressure and the residue thus obtained was purified by column chromatography using 20% ethyl acetate in hexane as eluant to furnish the title compound (240 mg).

Workup

  1. customTo the resulting reaction mixture
  2. stirringthe mixture was further stirred for 30 minutes at 0° C.
  3. stirringby stirring at room temperature for 30 minutes and finally at 80° C. for about 5-6 hours
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue thus obtained
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with water and brine
  8. dry with materialdried over anhydrous sodium sulphate
  9. filtrationfiltered
  10. customThe solvent was evaporated under reduced pressure
  11. customthe residue thus obtained
  12. customwas purified by column chromatography

Sources & evidence

ORD record
ord-d6ea9cdf44dd4640bbd9042fccb4732c
Source dataset
uspto-grants-2014_04
Patent number
US08710261B2

Reaction notes

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