HCID 19975456, compound → HCID 19975471, compound

HRID 1450248Notes

Reaction equation

HRID 1450248 reaction equation
[CH2:1]([Mg]Br)[CH3:2].[CH3:5][C:6]1([CH3:26])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:16]#[C:17][C:18]3[CH:23]=[CH:22][C:21]([CH:24]=[O:25])=[CH:20][N:19]=3)[CH:14]=2)[O:9][CH2:8][CH2:7]1>CCOCC>[CH3:5][C:6]1([CH3:26])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:16]#[C:17][C:18]3[CH:23]=[CH:22][C:21]([CH:24]([OH:25])[CH2:1][CH3:2])=[CH:20][N:19]=3)[CH:14]=2)[O:9][CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 19975456HCID 19975456, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 19975471HCID 19975471, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Four ml of a 3M (12 mmol) solution of ethylmagnesium bromide in ether is placed in a B-necked flask fitted with a mechanical stirrer, a reflux condenser protected by a drying tube and a pressure-equalizing dropping funnel protected by a drying tube. The flask is cooled in an ice bath and a solution of 2.8 g (10 mmol) of 2-(2-(4,4-Dimethylchroman-6-yl) ethynyl)-pryidine-5-carboxaldehyde in 10 ml of dry ether is added slowly with vigorous stirring. The cooling bath is then removed and the mixture heated at reflux for 3 hours. The mixture is then cooled in an ice-salt bath and 5 ml of saturated ammonium chloride solution added. The mixture is stirred for a further 1 hour and then filtered and the residue washed with two 10 ml portions of ether. The ether solution is then separated, dried (MgSO4) and the ether removed in vacuo. The residue is then purified by chromatography followed by recrystallization to give the title compound.

Workup

  1. customfitted with a mechanical stirrer, a reflux condenser
  2. customprotected by a drying tube
  3. customprotected by a drying tube
  4. temperatureThe flask is cooled in an ice bath
  5. customThe cooling bath is then removed
  6. temperaturethe mixture heated
  7. temperatureat reflux for 3 hours
  8. temperatureThe mixture is then cooled in an ice-salt bath
  9. addition5 ml of saturated ammonium chloride solution added
  10. filtrationfiltered
  11. washthe residue washed with two 10 ml portions of ether
  12. customThe ether solution is then separated
  13. dry with materialdried (MgSO4)
  14. customthe ether removed in vacuo
  15. customThe residue is then purified by chromatography
  16. customfollowed by recrystallization

Sources & evidence

ORD record
ord-048ff7a69c154537b2e55e1bfe37e5be
Source dataset
uspto-grants-1997_02
Patent number
US05602130

Reaction notes

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