Pyridine → HCID 59018085, compound

HRID 970186Notes

Reaction equation

HRID 970186 reaction equation
[O:1]=[C:2]([C:8]([O-:10])=[O:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH3:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:16][CH:15]=1)=[O:13].N1C=CC=[CH:30][CH:29]=1>>[OH:1][C:2]([CH2:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:16][CH:15]=1)=[O:13])([C:8]([O:10][CH2:29][CH3:30])=[O:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

4

Reactant 3

HCID 1049PyridineHCID 2452261-[4-(Benzyloxy)phenyl]ethan-1-oneHCID 20976715HCID 20976715, compound

Product 1

HCID 59018085HCID 59018085, compound

Procedure

19 cm3 of ethyl ketomalonate and 2.5 cm3 of pyridine were added to 23.1 g of 4-benzyloxyacetophenone. The reaction medium was heated and maintained at reflux for 12 hours. After cooling, the reaction medium was purified by chromatography on silica gel (particle size 40-63 μm, under an argon pressure of 150 kPa), eluting with a mixture of dichloromethane and methanol (99/1 by volume). The fractions containing the product were combined and then concentrated under reduced pressure (45° C.; 5 kPa). The product obtained was triturated in 150 cm3 of ethanol, filtered through a sinter funnel, washed with twice 50 cm3 of ethanol and 50 cm3 of isopropyl ether to give, after drying under reduced pressure (2 kPa; 55° C.), 5.6 g of diethyl hydroxy[2-(4-benzyloxyphenyl)-2-oxoethyl]malonate melting at 80° C.

Workup

  1. temperatureThe reaction medium was heated
  2. temperaturemaintained
  3. temperatureat reflux for 12 hours
  4. temperatureAfter cooling
  5. customthe reaction medium was purified by chromatography on silica gel (particle size 40-63 μm
  6. washunder an argon pressure of 150 kPa), eluting with a mixture of dichloromethane and methanol (99/1 by volume)
  7. additionThe fractions containing the product
  8. concentrationconcentrated under reduced pressure (45° C.; 5 kPa)
  9. customThe product obtained
  10. customwas triturated in 150 cm3 of ethanol
  11. filtrationfiltered through a sinter funnel
  12. washwashed with twice 50 cm3 of ethanol and 50 cm3 of isopropyl ether
  13. customto give
  14. dry with materialafter drying under reduced pressure (2 kPa; 55° C.), 5.6 g of diethyl hydroxy[2-(4-benzyloxyphenyl)-2-oxoethyl]malonate melting at 80° C.

Sources & evidence

ORD record
ord-4265da2df4da4af1a193611b9b402c57
Source dataset
uspto-grants-2007_12
Patent number
US07309701B2

Reaction notes

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