Potassium Carbonate → HCID 19913843, compound

HRID 1090785Notes

Reaction equation

HRID 1090785 reaction equation
[OH:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][CH2:7][C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1.Br[CH2:21][C:22]1[C:31]2[O:30][C:29]([C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:28][C:27](=[O:37])[C:26]=2[CH:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.C(OC(=O)C)C>[C:32]([C:29]1[O:30][C:31]2[C:22]([CH2:21][O:1][C:2]3[CH:3]=[CH:4][C:5]([O:6][CH2:7][C:8]4[CH:17]=[CH:16][C:15]5[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=5)[N:9]=4)=[CH:18][CH:19]=3)=[CH:23][CH:24]=[CH:25][C:26]=2[C:27](=[O:37])[CH:28]=1)([O:34][CH2:35][CH3:36])=[O:33]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 109887374-[(Quinolin-2-yl)methoxy]phenolHCID 19913877HCID 19913877, compound

Product 1

HCID 19913843HCID 19913843, compoundYield 28.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.8 g of 2-(4-hydroxyphenoxy)methylquinoline, 2.2 g of 8-bromomethyl-2-carboethoxy-4-oxo-4H-1-benzopyran and 1.0 g of potassium carbonate are combined in 100 ml of acetone and refluxed for 18 hours. The mixture is cooled, diluted with ethylacetate and filtered. The filtrate is concentrated and the crude product purified by flash chromatography on silica gel in 5% ethanol in chloroform/hexane (1:1) to give 0.96 g 2-carboethoxy-8-(4- (quinolin-2-yl-methoxy)phenoxymethyl)-4-oxo-4H-1-benzopyran: m.p. 124°-27° C.

Workup

  1. temperaturerefluxed for 18 hours
  2. temperatureThe mixture is cooled
  3. filtrationfiltered
  4. concentrationThe filtrate is concentrated
  5. customthe crude product purified by flash chromatography on silica gel in 5% ethanol in chloroform/hexane (1:1)

Sources & evidence

ORD record
ord-a162e8d6f6464dc7bf76968815380784
Source dataset
uspto-grants-1992_01
Patent number
US05082849

Reaction notes

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