Potassium Carbonate → HCID 10409943, compound

HRID 1656487Notes

Reaction equation

HRID 1656487 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-bf7c1473f40a475f9734a0fd098534b6
Source dataset
uspto-grants-1993_10
Patent number
US05254581

Reaction notes

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