Cyclopentanol → HCID 22145790, compound

HRID 993288Notes

Reaction equation

HRID 993288 reaction equation
[H-].[Na+].[CH:3]1([OH:8])[CH2:7][CH2:6][CH2:5][CH2:4]1.Cl[C:10]1[N:15]=[C:14]([C:16]([O:18][CH:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)=[O:17])[CH:13]=[CH:12][C:11]=1[O:24][CH3:25].[Cl-].[NH4+]>O1CCCC1>[CH:3]1([O:8][C:10]2[N:15]=[C:14]([C:16]([O:18][CH:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)=[O:17])[CH:13]=[CH:12][C:11]=2[O:24][CH3:25])[CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 7298CyclopentanolHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 22145838HCID 22145838, compound

Product 1

HCID 22145790HCID 22145790, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (887 mg of a 60% dispersion in oil) is added to a solution of cyclopentanol (3.35 mL) in dry tetrahydrofuran (127 mL) and the mixture stirred for 1.5 hours. Cyclopentyl 6-chloro-5-methoxypyridine-2-carboxylate (6.3 g) is added and the mixture is stirred at room temperature for 21 hours. The mixture is poured into saturated aqueous ammonium chloride (500 mL) and the resulting mixture extracted with ethyl acetate (2×500 mL). The combined extracts are washed with saturated aqueous sodium bicarbonate (500 mL) and water (500 mL). After drying (MgSO4) the solution is evaporated to dryness to give a yellow oil which is purified by flash chromatography (silica with pentane/ethyl acetate 9:1 v/v as eluent) affording cyclopentyl 6-cyclopentyloxy-5-methoxypyridine-2-carboxylate (3.6 g) as an oil.

Workup

  1. stirringthe mixture is stirred at room temperature for 21 hours
  2. extractionthe resulting mixture extracted with ethyl acetate (2×500 mL)
  3. washThe combined extracts are washed with saturated aqueous sodium bicarbonate (500 mL) and water (500 mL)
  4. dry with materialAfter drying (MgSO4) the solution
  5. customis evaporated to dryness
  6. customto give a yellow oil which
  7. customis purified by flash chromatography (silica with pentane/ethyl acetate 9:1 v/v as eluent)

Sources & evidence

ORD record
ord-6008a9e320114ba0a04924a54a71197b
Source dataset
uspto-grants-2002_10
Patent number
US06472412B1

Reaction notes

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