Lithium Hydroxide → Lithium 3-methylenecyclopentanecarboxylate

HRID 331108Notes

Reaction equation

HRID 331108 reaction equation
[CH2:1]=[C:2]1[CH2:6][CH2:5][CH:4]([C:7]([O:9]CC)=[O:8])[CH2:3]1.[OH-].[Li+:13]>C1COCC1.O>[CH2:1]=[C:2]1[CH2:6][CH2:5][CH:4]([C:7]([O-:9])=[O:8])[CH2:3]1.[Li+:13]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 13350809Ethyl 3-methylenecyclopentanecarboxylate

Product 1

HCID 67113791Lithium 3-methylenecyclopentanecarboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of ethyl 3-methylenecyclopentanecarboxylate (900 mg, 5.84 mmol) and lithium hydroxide (280 mg, 11.67 mmol) in THF (15 mL) and water (6 mL) was heated at 65° C. for 18 hours. Analysis by TLC indicated that the starting ester had been completely consumed. The organic solvents were removed via rotary evaporator, and the remaining aqueous solution was freeze-dried to yield lithium 3-methylenecyclopentanecarboxylate. 1H NMR (400 MHz, CD3OD) δ ppm 4.84-4.73 (m, 2H), 2.71-2.59 (m, 1H), 2.57-2.35 (m, 3H), 2.29-2.16 (m, 1H), 2.01-1.91 (1H, m), 1.84-1.72 (m, 1H,).

Workup

  1. customhad been completely consumed
  2. customThe organic solvents were removed via rotary evaporator
  3. customthe remaining aqueous solution was freeze-dried

Sources & evidence

ORD record
ord-c13ce5e1d3b947febcd9c8618e682d89
Source dataset
uspto-grants-2014_11
Patent number
US08877749B2

Reaction notes

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