Water → HCID 21198284, compound

HRID 1420568Notes

Reaction equation

HRID 1420568 reaction equation
[OH:1][CH:2]([CH2:8][CH:9]([CH3:11])[CH3:10])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[F:12][C:13]1[N:18]=[C:17]([F:19])[C:16]([F:20])=[C:15](F)[C:14]=1[F:22].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C.C(OCC)(=O)C>[CH2:6]([O:5][C:3]([CH:2]([O:1][C:15]1[C:14]([F:22])=[C:13]([F:12])[N:18]=[C:17]([F:19])[C:16]=1[F:20])[CH2:8][CH:9]([CH3:10])[CH3:11])=[O:4])[CH3:7]

Participants

7

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 69690PentafluoropyridineHCID 112030Ethyl 2-hydroxy-4-methylpentanoate

Product 1

HCID 21198284HCID 21198284, compoundYield 112.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 2-hydroxy-4-methylvalerate (0.50 g, 2.5 mmol) in dry DMF (25 mL) was added pentafluoropyridine (0.31 mL, 0.47 g, 2.8 mmol) and cesium carbonate (1.1 g, 3.3 mmol). The resultant mixture was heated to 45° C. and stirred at that temperature for 10 days, then poured into 100 mL of water and 100 mL of ethyl acetate. The aqueous layer was separated and extracted with another 500 mL of ethyl acetate. The combined organic extracts were shed with water (100 mL) then brine (100 mL), dried over MgSO4, filtered, and concentrated in vacuo to afford 0.87 g (99% yield) of 4-(1-ethoxycarbonyl-3-methylbutyl)oxy-2,3,5,6-tetrafluoropyridine as a clear, yellow liquid: NMR (CDCl3) 5.2 (d, 1), 4.3-4.1 (m, 3), 2.0 (m, 1), 1.8 (m, 1), 1.3 (m, 3), 1.0 (m, 6) ppm.

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted with another 500 mL of ethyl acetate
  3. dry with materialbrine (100 mL), dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-30952180136c4d169f786189ff7e0b04
Source dataset
uspto-grants-2000_06
Patent number
US06071912

Reaction notes

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