Water → HCID 46842252, compound

HRID 2227467Notes

Reaction equation

HRID 2227467 reaction equation
[CH3:1][O:2][C:3](=[O:26])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][C:13]2[N:14]=[C:15]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[O:16][C:17]=2[CH3:18])=[CH:6][C:5]=1[OH:25].C([O-])([O-])=O.[K+].[K+].[CH2:33](I)[CH3:34].O>CN(C=O)C.CCCCCC.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:26])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][C:13]2[N:14]=[C:15]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[O:16][C:17]=2[CH3:18])=[CH:6][C:5]=1[O:25][CH2:33][CH3:34]

Participants

8

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 22087445HCID 22087445, compound

Product 1

HCID 46842252HCID 46842252, compoundYield 96.6%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the compound 25 (0.27 g) in DMF (5 mL) was added K2CO3 (0.16 g) and EtI (0.07 mL) and the mixture was allowed to stand over night. The reaction mixture was poured into water and the product was extracted with ethyl acetate (30 mL). The ethyl acetate phase was washed with water, satd. NaCl and dried over anhydrous Na2SO4 and filtrated. Evaporation of the filtered gave a residue, from which 0.28 g (96.6%) of the colorless objective compound was obtained by silicagel column chromatography (ethyl acetate:n-hexane=1:3).

Workup

  1. waitto stand over night
  2. extractionthe product was extracted with ethyl acetate (30 mL)
  3. washThe ethyl acetate phase was washed with water
  4. dry with materialNaCl and dried over anhydrous Na2SO4
  5. filtrationfiltrated
  6. customEvaporation of the filtered
  7. customgave a residue

Sources & evidence

ORD record
ord-81eb1e64bd664413b1fc86bc2d7d4616
Source dataset
uspto-grants-2002_07
Patent number
US06414001B2

Reaction notes

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