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

HRID 1892997Notes

Reaction equation

HRID 1892997 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+]>CCOCC.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 ether (500 mL) at 0° C., followed by H2O (1.35 mL, 75.0 mmol) and was vigorously stirred overnight at rt. The reaction mixture was poured in a mixture of ice and water and washed with ether (3×). The aqueous layer was acidified with a 10% aq. citric acid solution at 0° C. and extracted with EtOAc (3×). The combined organic layers were washed with water (2×), brine, dried (MgSO4) and concentrated in vacuo to afford the titled product as a pale yellow oil (10 g, 46.8 mmol, 69% yield).

Workup

  1. washwashed with ether (3×)
  2. customwas acidified with a 10% aq. citric acid solution at 0° C.
  3. extractionextracted with EtOAc (3×)
  4. washThe combined organic layers were washed with water (2×), brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-189914c1079d470a95d1b238e31a1df8
Source dataset
uspto-grants-2013_08
Patent number
US08507722B2

Reaction notes

Loading…