Dimethyl Carbonate → HCID 68528872, compound

HRID 1036365Notes

Reaction equation

HRID 1036365 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]2[C:6](=[O:11])[CH2:7][CH2:8][CH2:9][CH2:10][C:2]1=2.[H-].[Na+].[CH3:14][O:15][C:16](=O)[O:17]C>>[O:11]=[C:6]1[C:3]2[CH:4]=[CH:5][O:1][C:2]=2[CH2:10][CH2:9][CH2:8][CH:7]1[C:16]([O:15][CH3:14])=[O:17]

Participants

4

Reactant 3

HCID 12021Dimethyl CarbonateHCID 24758Sodium hydrideHCID 12594359HCID 12594359, compound

Product 1

HCID 68528872HCID 68528872, compound

Procedure

5,6,7,8-Tetrahydro-cyclohepta[b]furan-4-one (J. Chem. Soc., Perkin Trans. 1, 1980, 2081-2083) (0.1 g, 0.7 mmol) in dimethylcarbonate (2 mL) was treated with a 60% dispersion of sodium hydride (0.06 g, 0.15 mmol) as described in Example 1A to yield the title product. NMR in CDCl3 indicates a 70:30 mixture of keto and enol forms: 1H NMR (300 MHz, CDCl3) δ 13.02 (s, 0.3H), 7.29 (d, J=2.03 Hz, 0.4H), 7.23 (d, J=2.03 Hz, 0.6H), 6.73 (d, J=2.03 Hz, 0.6H), 6.72 (d, J=2.03 Hz, 0.4H) 3.78 (s, 1.2H), 3.75 (s, 1.8H), 3.72 (dd, J=9.99, 3.9 Hz, 0.6H), 3.02 (m, 1.2H), 2.96 (t, J=6.6 Hz, 0.8H), 2.56 (t, 0.8H), 1.84-2.2 (m, 3.5H); MS (DCI/NH3) m/z 209 (M+H)+.

Sources & evidence

ORD record
ord-bd2e21c7316043efbfba2572f1a65532
Source dataset
uspto-grants-2013_10
Patent number
US08546410B2

Reaction notes

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