Hydrochloric Acid → 1-(Cyclopropylmethyl)cyclobutane-1-carboxylic acid

HRID 250539Notes

Reaction equation

HRID 250539 reaction equation
[Li+].CC([N-]C(C)C)C.[CH:9]1([C:13]([OH:15])=[O:14])[CH2:12][CH2:11][CH2:10]1.BrC[CH2:18][CH:19]1[CH2:21][CH2:20]1.Cl>C1COCC1>[CH:19]1([CH2:18][C:9]2([C:13]([OH:15])=[O:14])[CH2:12][CH2:11][CH2:10]2)[CH2:21][CH2:20]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 19494Cyclobutanecarboxylic acidHCID 2724682Lithium diisopropylamideHCID 22636989(2-Bromoethyl)cyclopropane

Product 1

HCID 450847861-(Cyclopropylmethyl)cyclobutane-1-carboxylic acidYield 124.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of LDA (100 ml, 2.0 M THF solution) in THF (100 ml) was added dropwise over a period of 20 minutes at 0° C., a solution of cyclobutane carboxylic acid (10 g, 0.1 mol) in THF (15 ml). The resulting mixture was stirred at RT for 2 h then bromoethylcyclopropane (15 g, 0.11 mol) was added dropwise and the mixture was stirred at RT. overnight. To the reaction mixture was added 2N HCl and the mixture was extracted with EtOAc. The organic layer was washed with water and brine to afford the title compound as light yellow oil (19.2 g), which was used in the next step without purification.

Workup

  1. stirringthe mixture was stirred at RT
  2. customovernight
  3. extractionthe mixture was extracted with EtOAc
  4. washThe organic layer was washed with water and brine

Sources & evidence

ORD record
ord-eb4e8a197f664120b13db0798cd0e72c
Source dataset
uspto-grants-2011_01
Patent number
US07863312B2

Reaction notes

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