Tetrahydrofuran → HCID 23103597, compound

HRID 2116510Notes

Reaction equation

HRID 2116510 reaction equation
C[Si](C)(C)CCOC[O:7][C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1.O.[C:17]1(C)[CH:22]=C[C:20](S(O)(=O)=O)=[CH:19][CH:18]=1.C(=O)(O)[O-].[Na+].[O:33]1[CH2:37][CH2:36][CH2:35][CH2:34]1>>[CH2:19]([C:18]1[CH:17]=[CH:22][C:36]([C:37]([C:13]2[CH:12]=[CH:11][N:10]=[CH:9][C:8]=2[OH:7])=[O:33])=[CH:35][CH:34]=1)[CH3:20]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 15635484HCID 15635484, compound

Product 1

HCID 23103597HCID 23103597, compoundYield 83%

Conditions

Temperature
80 °C

Procedure

Next, a mixture of 4-(4-ethylbenzoyl)-[3-[2-(trimethylsilyl)ethoxymethoxy]pyridine (3.4 g), p-toluenesulfonic acid monohydrate (3.46 g, 18.2 mmol) and tetrahydrofuran (60 mL) was stirred at 80° C. for 2 hours. After cooling to room temperature, the reaction mixture was poured into saturated aqueous sodium bicarbonate and extracted twice with ethyl acetate. The organic layers were dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:50) to give the titled compound (1.57 g, 83%).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted twice with ethyl acetate
  3. dry with materialThe organic layers were dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:50)

Sources & evidence

ORD record
ord-f7ab48af33784c559dc8887e81b5e0aa
Source dataset
uspto-grants-2008_10
Patent number
US07439232B2

Reaction notes

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