Water → HCID 57629444, compound

HRID 2108854Notes

Reaction equation

HRID 2108854 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][CH:12]=[C:11]([C:17]([F:20])([F:19])[F:18])[CH:10]=2)=[O:5])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][O:33][C:34]1[C:35](=[O:42])[CH:36]=[C:37]([CH2:40][OH:41])[O:38][CH:39]=1.O>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[O:16][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][O:33][C:34]1[C:35](=[O:42])[CH:36]=[C:37]([CH2:40][OH:41])[O:38][CH:39]=1)=[CH:13][CH:12]=[C:11]([C:17]([F:20])([F:18])[F:19])[CH:10]=2)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 179758375-(5-Bromopentyloxy)-2-(hydroxymethyl)-4H-pyran-4-oneHCID 178469560HCID 178469560, compound

Product 1

HCID 57629444HCID 57629444, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

4-Hydroxy-7-trifluoromethyl-quinoline-3-carboxylic acid ethyl ester (0.86 g, 3.02 mmol) was dissolved in DMF (10 mL). Cs2CO3 (0.98 g, 3.02 mmol) was added at RT and the mixture was stirred for 10 min. A solution of 5-(5-bromo-pentyloxy)-2-hydroxymethyl-pyran-4-one 10 (0.86 g, 3.02 mmol) in DMF (5 mL) was added via syringe. This mixture was stirred at 50° C. for 22 h. Water (10 mL) was added and the mixture extracted with EtOAc (2×50 mL), washed with water (3×50 mL), brine (3×50 mL) dried over MgSO4, filtered and evaporated. The crude product was purified by column chromatography on silica using as eluent (CH2Cl2:MeOH)=90:10. 4-[5-(6-Hydroxymethyl-4-oxo-4H-pyran-3-yloxy)-pentyloxy]-7-trifluoromethyl-quinoline-3-carboxylic acid ethyl ester 13 was obtained (0.43 g, 31% yield) as a pale yellow foam.

Workup

  1. stirringThis mixture was stirred at 50° C. for 22 h
  2. extractionthe mixture extracted with EtOAc (2×50 mL)
  3. washwashed with water (3×50 mL), brine (3×50 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by column chromatography on silica using as eluent (CH2Cl2:MeOH)=90:10

Sources & evidence

ORD record
ord-a07bd55c87614e92be1e5d24a5f4608d
Source dataset
uspto-grants-2009_04
Patent number
US07514432B2

Reaction notes

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