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

HRID 556885Notes

Reaction equation

HRID 556885 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 bromoethyl cyclopropane (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 overnight
  2. extractionthe mixture was extracted with EtOAc
  3. washThe organic layer was washed with water and brine

Sources & evidence

ORD record
ord-ac5a33ba1811473792cd25ccfa4d4ae7
Source dataset
uspto-grants-2011_11
Patent number
US08058305B2

Reaction notes

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