Water → 5-(5-(6-(trifluoromethyl)quinolin-4-yloxy)pentyloxy)-2-(hydroxymethyl)-4H-pyran-4-one

HRID 2108852Notes

Reaction equation

HRID 2108852 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[OH:13].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][O:28][C:29]1[C:30](=[O:37])[CH:31]=[C:32]([CH2:35][OH:36])[O:33][CH:34]=1.O>CN(C=O)C>[F:15][C:2]([F:1])([F:14])[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[O:13][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][O:28][C:29]1[C:30](=[O:37])[CH:31]=[C:32]([CH2:35][OH:36])[O:33][CH:34]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 179758375-(5-Bromopentyloxy)-2-(hydroxymethyl)-4H-pyran-4-oneHCID 1785164066-(Trifluoromethyl)-4-quinolinol

Product 1

HCID 179758165-(5-(6-(trifluoromethyl)quinolin-4-yloxy)pentyloxy)-2-(hydroxymethyl)-4H-pyran-4-oneYield 21%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

6-Trifluoromethyl-quinolin-4-ol (0.23 g, 1.08 mmol) was dissolved in DMF (3 mL). Cs2CO3 (0.35 g, 1.08 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 (0.30 g, 1.03 mmol) in DMF (2 mL) was added via syringe. This mixture was stirred at 50° C. for 1 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. 5-(5-(6-(trifluoromethyl)quinolin-4-yloxy)pentyloxy)-2-(hydroxymethyl)-4H-pyran-4-one 11 was obtained (93 mg, 21% yield) as a yellow oil.

Workup

  1. stirringThis mixture was stirred at 50° C. for 1 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-e95b5aa6e6064b3c9cfe6e278adcd554
Source dataset
uspto-grants-2009_04
Patent number
US07514432B2

Reaction notes

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