Dimethyl Carbonate → HCID 68603292, compound

HRID 2386996Notes

Reaction equation

HRID 2386996 reaction equation
[C:1]1([CH:7]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9](=[O:14])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:15](=O)([O:18]C)[O:16][CH3:17].[H-].[Na+]>CO>[O:14]=[C:9]1[CH2:8][CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:13][CH2:12][CH2:11][CH:10]1[C:15]([O:16][CH3:17])=[O:18]

Participants

5

Reactant 3

HCID 12021Dimethyl CarbonateHCID 24758Sodium hydrideHCID 1129841674395-08-7

Product 1

HCID 68603292HCID 68603292, compound

Reagents, catalysts & solvents 1

HCID 887MethanolCatalyst

Procedure

A mixture of 3-phenylcycloheptanone (1.88 g, 9.99 mmol) and 5 drops of methanol in dimethyl carbonate (1.68 mL, 20.0 mmol) was treated with sodium hydride (60% dispersion, 800 mg, 20.0 mmol). The reaction was then refluxed for 2 hours before being cooled back to room temperature. The reaction was quenched with 2 M hydrochloric acid and extracted with ether, then chromatographed on silica gel (15% ethyl acetate/hexane, eluant) to afford the title compound as a colorless oil. 1H NMR (300 MHz, DMSO-d6) δ 7.26 (m, 5H), 3.81 (dd, J=11.70, 3.77 Hz, 1H), 3.63 (s, 3H), 3.17 (m, 2H), 1.86 (m, 6H); MS (DCI+) m/z 247 (M+H)+, 264 (M+NH4)+.

Workup

  1. temperatureThe reaction was then refluxed for 2 hours
  2. customThe reaction was quenched with 2 M hydrochloric acid
  3. extractionextracted with ether
  4. customchromatographed on silica gel (15% ethyl acetate/hexane, eluant)

Sources & evidence

ORD record
ord-40b3c5e895ee4e36a782b4f22cc35dcb
Source dataset
uspto-grants-2012_09
Patent number
US08268846B2

Reaction notes

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