Hydrochloric Acid → Methyl 3-oxoheptanoate

HRID 865000Notes

Reaction equation

HRID 865000 reaction equation
[C:1]([O:7][CH3:8])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[CH2:9]([Li])[CH2:10][CH2:11]C.C(I)CC.Cl>CCCCCC.O>[O:4]=[C:3]([CH2:5][CH2:9][CH2:10][CH3:11])[CH2:2][C:1]([O:7][CH3:8])=[O:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7757Methyl acetoacetateHCID 336431-IodopropaneHCID 178418339Butyllithium

Product 1

HCID 546075Methyl 3-oxoheptanoateYield 61%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8058HexaneSolvent

Procedure

After stirring for 20 minutes, 9.3 ml of methyl acetoacetate were dropped, stirring was continued for 30 minutes at 0° C. and further 54 ml of butyllithium 1.6M in hexane were dropped. After further 30 minutes 8.4 ml of propyl iodide were dropped into the dark orange solution. The temperature was allowed to raise to room temperature and after 30 minutes, 50 ml of 37% HCl diluted with 100 ml of H2O were continuously dropped while keeping the temperature under 15° C. The reaction mixture was extracted with Et2O. The organic phase was washed with a NaCl saturated solution, dried on Na2SO4 and evaporated to dryness. The residue was purified by FC (eluent: AcOEt/hexane 1:9). 8.3 g of a clear oil were obtained (yield 61%); 1H-NMR (200 MHz, CDCl3)δ: 0.90 (t, 3H), 1.22-1.65 (m, 4H), 2.53 (t, 2H), 3.44 (s, 2H), 3.73 (s, 3H).

Workup

  1. stirringstirring
  2. waitwas continued for 30 minutes at 0° C.
  3. additionwere continuously dropped
  4. customunder 15° C
  5. extractionThe reaction mixture was extracted with Et2O
  6. washThe organic phase was washed with a NaCl saturated solution
  7. customdried on Na2SO4
  8. customevaporated to dryness
  9. customThe residue was purified by FC (eluent: AcOEt/hexane 1:9)

Sources & evidence

ORD record
ord-84a4f1b15e46462fbfc21fdb699c82c8
Source dataset
uspto-grants-1996_10
Patent number
US05565464

Reaction notes

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