Potassium Carbonate → HCID 10409943, compound

HRID 1654499Notes

Reaction equation

HRID 1654499 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH3:13])[C:8](=[O:14])[CH:7]=[CH:6]2.[CH2:15]([O:17][C:18]([C:20]1([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([OH:32])[CH:27]=2)[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)=[O:19])[CH3:16].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:15]([O:17][C:18]([C:20]1([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH2:2][C:3]3[CH:4]=[C:5]4[C:10](=[CH:11][CH:12]=3)[N:9]([CH3:13])[C:8](=[O:14])[CH:7]=[CH:6]4)[CH:27]=2)[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)=[O:19])[CH3:16]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 10083449HCID 10083449, compoundHCID 151990656-(Bromomethyl)-1-methylquinolin-2(1H)-one

Product 1

HCID 10409943HCID 10409943, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-bromomethyl-1-methyl-1,2-dihydroquinolin-2-one (0.1 g), 4-ethoxycarbonyl-4-(3-hydroxyphenyl)tetrahydropyran (0.098 g), potassium carbonate (0.057 g) and DMF (2 ml) was stirred at ambient temperature for 16 hours. The mixture was partitioned between diethyl ether and 0.5N aqueous hydrochloric acid. The organic layer was washed with water and brine, dried (MgSO4) and evaporated. The residue was purified by column chromatography using initially methylene chloride and then increasingly polar mixtures of methylene chloride and acetone as eluent. There was thus obtained an oil which was triturated in pentane to give 4-ethoxycarbonyl-4-[3-(1-methyl-2-oxo-1,2-dihydroquinolin-6-ylmethoxy)phenyl]tetrahydropyran (0.099 g, 60%), m.p. 109°-110° C.

Workup

  1. customThe mixture was partitioned between diethyl ether and 0.5N aqueous hydrochloric acid
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue was purified by column chromatography
  6. temperatureincreasingly polar mixtures of methylene chloride and acetone as eluent
  7. customThere was thus obtained an oil which
  8. customwas triturated in pentane

Sources & evidence

ORD record
ord-dee74f46ef9f480d962a81bb002a208e
Source dataset
uspto-grants-1995_04
Patent number
US05407945

Reaction notes

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