Dimethyl Carbonate → HCID 68800424, compound

HRID 2059762Notes

Reaction equation

HRID 2059762 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]21[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C:10]2=[O:16].[C:17](=O)([O:20]C)[O:18][CH3:19].[H-].[Na+]>CO>[O:16]=[C:10]1[C:2]2([CH2:1][C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH2:3]2)[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]1[C:17]([O:18][CH3:19])=[O:20]

Participants

5

Reactant 3

HCID 12021Dimethyl CarbonateHCID 24758Sodium hydrideHCID 68797590HCID 68797590, compound

Product 1

HCID 68800424HCID 68800424, compound

Reagents, catalysts & solvents 1

HCID 887MethanolCatalyst

Procedure

A mixture of Example 19A (1.8 g, 8.40 mmol) in dimethyl carbonate (7.1 mL, 84 mmol) was treated with sodium hydride (60% dispersion in mineral oil, 0.672 g, 16.80 mmol) and a catalytic amount of MeOH (2 drops), then the mixture was heated at reflux. After 3 hours, the reaction was cooled to room temperature, and then it was quenched with 2N HCl. The mixture was extracted with ether, then the extracts were dried (Na2SO4) and evaporated. Purification by silica gel chromatography (10 to 25% EtOAc-hexane, eluant) afforded the title compound. 1H NMR (300 MHz, DMSO-d6) δ 7.10-7.21 (m, 4H), 4.25 (dd, J=11.1, 2.8 Hz, 1H), 3.57 (s, 3H), 3.51 (d, J=15.9 Hz, 1H), 3.15 (d, J=15.9 Hz, 1H), 3.00 (m, 1H), 2.60 (d, J=16.3 Hz, 1H), 2.09 (m, 1H), 1.90 (d, J=5.2 Hz, 2H), 1.72-1.85 (m, 2H), 1.44-1.56 (m, 2H), 1.02-1.15 (m, 1H). MS (DCI+) m/z 273 (M+H), 290 (M+NH4).

Workup

  1. temperatureat reflux
  2. customit was quenched with 2N HCl
  3. extractionThe mixture was extracted with ether
  4. dry with materialthe extracts were dried (Na2SO4)
  5. customevaporated
  6. customPurification by silica gel chromatography (10 to 25% EtOAc-hexane, eluant)

Sources & evidence

ORD record
ord-cd86a70d52a34e5eb6ea56881aca4695
Source dataset
uspto-grants-2012_10
Patent number
US08278313B2

Reaction notes

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