Diethyl Carbonate → HCID 69491010, compound

HRID 1768132Notes

Reaction equation

HRID 1768132 reaction equation
[H-].[Na+].C(O[C:6](=[O:10])[O:7][CH2:8][CH3:9])C.[F:11][C:12]1[CH:13]=[C:14]([CH:29]=[CH:30][CH:31]=1)[CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]2[CH2:27][CH2:26][CH2:25][C:24]2=[O:28])=[CH:19][CH:18]=1>C1COCC1>[CH2:8]([O:7][C:6]([CH:25]1[CH2:26][CH2:27][N:23]([C:20]2[CH:21]=[CH:22][C:17]([O:16][CH2:15][C:14]3[CH:29]=[CH:30][CH:31]=[C:12]([F:11])[CH:13]=3)=[CH:18][CH:19]=2)[C:24]1=[O:28])=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 7766Diethyl CarbonateHCID 24758Sodium hydrideHCID 23614758HCID 23614758, compound

Product 1

HCID 69491010HCID 69491010, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

370 mg (15.4 mmol) sodium hydride is suspended in 20 ml THF and 911 mg (7.7 mmol) diethylcarbonate is added. The suspension is heated to reflux temperature. A solution of 2.0 g (7.0 mmol) 1-[4-(3-Fluoro-benzyloxy)-phenyl]-pyrrolidin-2-one in 10 ml THF is slowly added into the boiling solution. The mixture is boiled for another 5 hours, then hydrolysed with cold water and washed successively with water, saturated sodium hydrogencarbonate solution, water and saturated sodium chloride solution. Chromatography (silica gel, dichloromethane/ethyl acetate) yields 1.3 g (52%) of a yellowish semisolid. MS: m/e=358.2 (M+H)+.

Workup

  1. temperatureThe suspension is heated
  2. temperatureto reflux temperature
  3. washhydrolysed with cold water and washed successively with water, saturated sodium hydrogencarbonate solution, water and saturated sodium chloride solution

Sources & evidence

ORD record
ord-b0c9f8377e4c444780fd4f4ce369227b
Source dataset
uspto-grants-2007_06
Patent number
US07235581B2

Reaction notes

Loading…