Di-tert-butyl 2-ethylcyclopropane-1,1-dicarboxylate → 1-(tert-Butoxycarbonyl)-2-ethylcyclopropane-1-carboxylic acid

HRID 1365007Notes

Reaction equation

HRID 1365007 reaction equation
[C:1]([O:5][C:6]([C:8]1([C:13]([O:15]C(C)(C)C)=[O:14])[CH2:10][CH:9]1[CH2:11][CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(C)([O-])C.[K+]>C(OCC)C.O>[C:1]([O:5][C:6]([C:8]1([C:13]([OH:15])=[O:14])[CH2:10][CH:9]1[CH2:11][CH3:12])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 13416307Di-tert-butyl 2-ethylcyclopropane-1,1-dicarboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 666701131-(tert-Butoxycarbonyl)-2-ethylcyclopropane-1-carboxylic acidYield 69%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

The product of Step 1 (18.3 g, 67.8 mmol) was added to a suspension of potassium tert-butoxide (33.55 g, 299.0 mmol) in dry diethyl ether (500 mL) at 0° C., treated with H2O (1.35 mL, 75.0 mmol), and was vigorously stirred overnight at room temperature. The reaction mixture was poured in a mixture of ice and water and washed with diethyl ether (3×). The aqueous layer was adjusted to acidic pH with a 10% aqueous citric acid solution at 0° C. and extracted with ethyl acetate (3×). The combined organic layers were washed with water (2×), brine, dried (MgSO4), filtered, and concentrated in vacuo to provide the desired product as a pale yellow oil (10 g, 46.8 mmol, 69% yield).

Workup

  1. washwashed with diethyl ether (3×)
  2. customwas adjusted to acidic pH with a 10% aqueous citric acid solution at 0° C.
  3. extractionextracted with ethyl acetate (3×)
  4. washThe combined organic layers were washed with water (2×), brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ea7c572279f44b3da62494e9a7746ee6
Source dataset
uspto-grants-2011_02
Patent number
US07888464B2

Reaction notes

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