Methane → HCID 9838237, compound

HRID 374447Notes

Reaction equation

HRID 374447 reaction equation
C([O:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12][N:11]([CH2:16][CH2:17][O:18][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])[C:10]=1[CH2:25][CH3:26])C1C=CC=CC=1.[H][H].C>CN(C)C=O.[Pd].C(OCC)(=O)C>[CH2:25]([C:10]1[N:11]([CH2:16][CH2:17][O:18][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])[CH:12]=[CH:13][C:14](=[O:15])[C:9]=1[OH:8])[CH3:26]

Participants

7

Reactant 3

HCID 297MethaneHCID 10546265HCID 10546265, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 9838237HCID 9838237, compoundYield 534.9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-benzyloxy-2-ethyl-1-(2-pivaloyloxyethyl)pyridin-4-one (0.5 g) in dimethylformamide (25 ml) was added 5% palladium on charcoal catalyst (0.1 g) and the reaction mixture was stirred at room temperature under a constant stream of hydrogen for 24 hours. The dimethylformamide was then removed under high vacuum by rotary evaporation to give an oil. The solid obtained on cooling the oil was dissolved in hot ethyl acetate and the solution treated with activated charcoal, refluxed for 5 minutes, filtered and rotary evaporated. The resultant residue was recrystalized from petroleum ether (boiling point 40°-60° C.) to give the title compound (2 g, 53%) as colourless crystals, m.p. 113°-115° C., νmax (nujol) 1580, 1630, 1725, 3130 cm-1 ; δ(90 MHz, CDCl3), 7.25 (1H, d), 6.43 (1H, d), 5.25 (1H, s, br), 4.29 (2H, t), 4.21 (2H, t), 2.85 (2H, q), 1.27 (3H, t), 1.28 (9H, s).

Workup

  1. customThe dimethylformamide was then removed under high vacuum by rotary evaporation
  2. customto give an oil
  3. customThe solid obtained
  4. temperatureon cooling the oil
  5. temperaturerefluxed for 5 minutes
  6. filtrationfiltered
  7. customThe resultant residue was recrystalized from petroleum ether (boiling point 40°-60° C.)

Sources & evidence

ORD record
ord-bc98bbd95d96460393f2fc1d19327c51
Source dataset
uspto-grants-1996_01
Patent number
US05480894

Reaction notes

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