Methyl iodide → HCID 10774268, compound

HRID 2202138Notes

Reaction equation

HRID 2202138 reaction equation
[CH3:1][C:2]1([CH3:13])[C:6]2([C:10]([OH:12])=[O:11])[C:7]([CH2:9][CH:3]1[CH2:4][CH2:5]2)=[O:8].[C:14]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C.O>[CH3:14][O:11][C:10]([C@@:6]12[C:2]([CH3:13])([CH3:1])[C@@H:3]([CH2:4][CH2:5]1)[CH2:9][C:7]2=[O:8])=[O:12]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 2978887,7-Dimethyl-2-oxobicyclo[2.2.1]heptane-1-carboxylic acid

Product 1

HCID 10774268HCID 10774268, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of ketopinic acid 6a 0.182 g (1 mmol) and K2CO3 1.1 g (8 mmol) stirred in DMF 10 ml was added MeI 0.125 ml (0.284 g, 2 mmol). The reaction mixture was allowed to stir for 18 hrs at ambient temperature. The reaction mixture was dissolved in water 80 ml and extracted with 3×30 ml portions of diethyl ether. The organic phase was washed with NaHCO3 saturated solution, dried over MgSO4 and concentrated in vacuo to give yellow oil 0.184 g (94%). 1H NMR (300 MHz, CDCl3) δ ppm 3.75 (s, 3H), 2.53 (ddd, J=18.29, 3.7 Hz, 1H), 2.36 (ddd, J=14.99, 11.82, 3.99 Hz, 1H), 2.10 (t, J=4.4 Hz, 1H), 2.02 (m, 1H), 1.92-1.98 (d, J=18.40 Hz, 1H), 1.79 (ddd, J=14.16, 9.35, 4.95 Hz, 1H), 1.41 (ddd, J=12.65, 9.49, 4.26 Hz, 1H), 1.15 (s, 3H), 1.07 (s, 3H). Exact mass calculated for C11H16O3 m/e 196.11. found 196.22.

Workup

  1. extractionextracted with 3×30 ml portions of diethyl ether
  2. washThe organic phase was washed with NaHCO3 saturated solution
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0872ceea240e4f5ab6e96649d64180df
Source dataset
uspto-grants-2016_06
Patent number
US09365534B2

Reaction notes

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