Water → HCID 66882028, compound

HRID 1893564Notes

Reaction equation

HRID 1893564 reaction equation
CN(C)C=O.[CH2:6]([O:8][C:9](=[O:26])[CH2:10][N:11]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:12]1[CH:17]=[C:16](I)[CH:15]=[CH:14][C:13]=1[CH3:19])[CH3:7].[C:27]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])(=[O:30])[CH:28]=[CH2:29].O>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C.C(N(CC)CC)C>[CH2:6]([O:8][C:9](=[O:26])[CH2:10][N:11]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:12]1[CH:17]=[C:16]([CH2:29][CH2:28][C:27]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH:15]=[CH:14][C:13]=1[CH3:19])[CH3:7]

Participants

8

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 15458tert-Butyl acrylateHCID 66880523HCID 66880523, compound

Product 1

HCID 66882028HCID 66882028, compoundYield 88%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To N,N-dimethylformamide (43 ml) were added the compound (2.03 g, 5.00 mmol) obtained in step A, tert-butyl acrylate (3.20 g, 25.00 mmol), [1,1′-bis(diphenylphosphino)ferrocene]palladium(II)dichloride—dichloromethane complex (1:1) (204 mg, 0.250 mmol), tetra-n-butylammoniumiodide (2.78 g, 7.50 mmol), water (6.9 ml) and triethylamine (6.9 ml), and the mixture was heated at 80° C. for 2 hr. The reaction mixture was cooled, diluted with ethyl acetate, washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, the solution was concentrated under reduced pressure, and the obtained oil was purified by silica gel column chromatography (ethyl acetate-hexane). To the obtained colorless oil (1.86 g) in ethanol (23 ml) was added 10% palladium carbon (containing water) (186 mg), and the mixture was stirred at room temperature for 3 hr. The insoluble material was filtered off, and the solution was concentrated under reduced pressure. The obtained oil was purified by silica gel column chromatography (ethyl acetate-hexane) to give the title compound (1.79 g, yield 88%) as a colorless oil.

Workup

  1. temperatureThe reaction mixture was cooled
  2. washwashed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe insoluble material was filtered off
  5. concentrationthe solution was concentrated under reduced pressure
  6. customthe obtained oil was purified by silica gel column chromatography (ethyl acetate-hexane)
  7. additionTo the obtained colorless oil (1.86 g) in ethanol (23 ml) was added 10% palladium carbon (containing water) (186 mg)
  8. filtrationThe insoluble material was filtered off
  9. concentrationthe solution was concentrated under reduced pressure
  10. customThe obtained oil was purified by silica gel column chromatography (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-e64322b3120b490c81b0df056bac0f2e
Source dataset
uspto-grants-2013_08
Patent number
US08513235B2

Reaction notes

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