Diethyl Carbonate → HCID 68597039, compound

HRID 884661Notes

Reaction equation

HRID 884661 reaction equation
[H-].[Na+].C(O[C:6](=O)[O:7][CH2:8][CH3:9])C.[Br:11][C:12]1[CH:13]=[CH:14][C:15]([O:21][CH2:22][O:23][CH3:24])=[C:16]([C:18](=[O:20])[CH3:19])[CH:17]=1.C1C[O:28]CC1>>[Br:11][C:12]1[CH:13]=[CH:14][C:15]([O:21][CH2:22][O:23][CH3:24])=[C:16]([C:18](=[O:20])[CH2:19][C:9](=[O:28])[CH2:8][O:7][CH3:6])[CH:17]=1

Participants

5

Reactant 4

HCID 7766Diethyl CarbonateHCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 57173995HCID 57173995, compound

Product 1

HCID 68597039HCID 68597039, compound

Conditions

Temperature
80 °C

Procedure

To a slurry of sodium hydride (60% oily dispersion; 1.49 g, 37 mmol) and diethylcarbonate (6.0 mL, 49 mmol) in anhydrous THF (70 mL), a solution of 1-(5-bromo-2-(methoxymethoxy)phenyl)ethanone (15, 4.435 g, 17.1 mmol) in anhydrous THF (30 mL) was added in one portion at rt under a nitrogen atmosphere. The mixture was stirred at 80° C. for 5 h. As the reaction was deemed complete by LC-MS, the mixture was cooled to room temperature and quenched by pouring it onto 1:1 ice/1N NaHSO4 (100 mL). Extractions with Et2O (2×150 mL) followed. The combined organic layers were washed with water (80 mL), brine (60 mL), and then dried over MgSO4. After purification by flash chromatography (9:1 to 8:2 hexane/EtOAc), the title compound (16) was obtained as colorless oil (4.403 g, 78% yield).

Workup

  1. temperaturethe mixture was cooled to room temperature
  2. customquenched
  3. additionby pouring it onto 1:1 ice/1N NaHSO4 (100 mL)
  4. extractionExtractions with Et2O (2×150 mL)
  5. washThe combined organic layers were washed with water (80 mL), brine (60 mL)
  6. dry with materialdried over MgSO4
  7. customAfter purification by flash chromatography (9:1 to 8:2 hexane/EtOAc)

Sources & evidence

ORD record
ord-b480de53421741c781eedd2e0e2ff9f2
Source dataset
uspto-grants-2012_08
Patent number
US08242129B2

Reaction notes

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