Iodoethane → Ethyl 3-methylidenecyclobutane-1-carboxylate

HRID 2042268Notes

Reaction equation

HRID 2042268 reaction equation
I[CH2:2][CH3:3].[CH2:4]=[C:5]1[CH2:8][CH:7]([C:9]([OH:11])=[O:10])[CH2:6]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH2:4]=[C:5]1[CH2:8][CH:7]([C:9]([O:11][CH2:2][CH3:3])=[O:10])[CH2:6]1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 274753-Methylenecyclobutanecarboxylic acid

Product 1

HCID 18706839Ethyl 3-methylidenecyclobutane-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Iodoethane (7.5 mL, 93.0 mol) was added at rt to a mixture of 3-methylenecyclobutanecarboxylic acid (10.0 g, 80.0 mmol) and cesium carbonate (56.0 g, 170.0 mmol) in anhydrous N,N-dimethylformamide (500.00 mL) under an atmosphere of nitrogen. The reaction was stirred for 16 hr then partitioned between diethyl ether (1 L) and brine (1 L). The aqueous layer was extracted with diethyl ether (3×500 mL) and the combined organic phases washed with water (2×1 L), dried over sodium sulfate, filtered and concentrated in vacuo to yield desired product 1H NMR (400 MHz, CDCl3) δ ppm 1.26 (t, 3H), 2.71-3.27 (m, 5H), 4.15 (q, J=7.07 Hz, 2H) and 4.53-4.96 (m, 2H).

Workup

  1. customthen partitioned between diethyl ether (1 L) and brine (1 L)
  2. extractionThe aqueous layer was extracted with diethyl ether (3×500 mL)
  3. washthe combined organic phases washed with water (2×1 L)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d2890bff2263436887ed91e96799d21c
Source dataset
uspto-grants-2013_11
Patent number
US08586546B2

Reaction notes

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