Dimethyl Carbonate → HCID 68923799, compound

HRID 2088713Notes

Reaction equation

HRID 2088713 reaction equation
[CH3:1][C:2]1([CH3:10])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=[O:9].[C:11](=O)([O:14]C)[O:12][CH3:13].[H-].[Na+]>CO>[CH3:1][C:2]1([CH3:10])[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]([C:11]([O:12][CH3:13])=[O:14])[C:3]1=[O:9]

Participants

5

Reactant 3

HCID 12021Dimethyl CarbonateHCID 24758Sodium hydrideHCID 12648913HCID 12648913, compound

Product 1

HCID 68923799HCID 68923799, compound

Reagents, catalysts & solvents 1

HCID 887MethanolCatalyst

Procedure

A mixture of Example 1A (2.104 g, 15.00 mmol) and 5 drops of MeOH in dimethyl carbonate (12.7 mL, 151 mmol) was treated with sodium hydride (60% dispersion, 1.200 g, 30.0 mmol). The reaction was then refluxed for 2 hours before being cooled back to room temperature. The reaction was quenched with 2M HCl and extracted with ether, then chromatographed on silica gel (3 to 12% EtOAc-hexane, eluant) to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ 4.15 (m, 1H), 3.58 (s, 3H), 2.02 (m, 1H), 1.61-1.77 (m, 5H), 1.30-1.44 (m, 2H), 1.11 (s, 3H), 1.01 (s, 3H). MS (DCI+) m/z 216 (M+H)+.

Workup

  1. temperatureThe reaction was then refluxed for 2 hours
  2. customThe reaction was quenched with 2M HCl
  3. extractionextracted with ether
  4. customchromatographed on silica gel (3 to 12% EtOAc-hexane, eluant)

Sources & evidence

ORD record
ord-02c158c00a9949588974a41715b25921
Source dataset
uspto-grants-2013_05
Patent number
US08436005B2

Reaction notes

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